EP2802335B1 - Use of avocado kernel to obtain avocado oil enriched in alkyl polyols and/or their acetylated derivatives - Google Patents

Use of avocado kernel to obtain avocado oil enriched in alkyl polyols and/or their acetylated derivatives Download PDF

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Publication number
EP2802335B1
EP2802335B1 EP13700382.8A EP13700382A EP2802335B1 EP 2802335 B1 EP2802335 B1 EP 2802335B1 EP 13700382 A EP13700382 A EP 13700382A EP 2802335 B1 EP2802335 B1 EP 2802335B1
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EP
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Prior art keywords
avocado
oil
alkyl polyols
acetylated derivatives
avocados
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EP13700382.8A
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German (de)
French (fr)
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EP2802335A1 (en
Inventor
Philippe Msika
Jacques Legrand
Sébastien Garnier
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Laboratoires Expanscience SA
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Laboratoires Expanscience SA
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Priority to PL13700382T priority Critical patent/PL2802335T3/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/54Lauraceae (Laurel family), e.g. cinnamon or sassafras
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00Production of fats or fatty oils from raw materials
    • C11B1/06Production of fats or fatty oils from raw materials by pressing
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L19/00Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/03Products from fruits or vegetables; Preparation or treatment thereof consisting of whole pieces or fragments without mashing the original pieces
    • A23L19/07Fruit waste products, e.g. from citrus peel or seeds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52Adding ingredients
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11Plant sterols or derivatives thereof, e.g. phytosterols
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115Fatty acids or derivatives thereof; Fats or oils
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/04Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/06Preparations for care of the skin for countering cellulitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00Production of fats or fatty oils from raw materials
    • C11B1/02Pretreatment
    • C11B1/04Pretreatment of vegetable raw material
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00Production of fats or fatty oils from raw materials
    • C11B1/06Production of fats or fatty oils from raw materials by pressing
    • C11B1/08Production of fats or fatty oils from raw materials by pressing by hot pressing
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00Preparations for use in therapy

Definitions

  • the present description relates to the use of avocado kernel to obtain an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives.
  • said avocado kernel represents 10 to 50% by mass, in particular 20 to 40% by mass, relative to the total mass of avocado used.
  • the objects of the invention are defined in the claims.
  • the invention relates to a process for obtaining an avocado oil enriched in alkyl polyols and / or their acetylated derivatives from at least avocado pits, said oil containing at least 0.5% by mass.
  • the invention also relates to an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, obtainable by this process, containing at least 0.5% by mass of alkyl polyols or their acetylated derivatives, relative to the total mass of the oil.
  • the present description also discloses the use of avocado oil for preparing an avocado oil concentrate enriched in alkyl polyols and / or in their acetylated derivatives, or for preparing an avocado unsaponifiable compound enriched in alkyl polyols.
  • the invention relates to an avocado unsaponifiable material enriched in alkyl polyols and / or their acetylated derivatives or else an avocado oil concentrate enriched in alkyl polyols and / or their acetylated derivatives, said concentrate containing at least 5 % of alkyl polyols and / or their acetylated derivatives by mass, relative to the total mass of the concentrate, said unsaponifiable and said oil concentrate being obtainable from said avocado oil, for its use as a medicament, advantageously in the prevention and / or treatment of connective tissue disorders such as osteoarthritis, joint pathologies such as rheumatism, or even periodontal diseases, such as gingivitis or periodontitis.
  • connective tissue disorders such as osteoarthritis, joint pathologies such as rheumatism, or even periodontal diseases, such as gingivitis or periodontitis.
  • avocado oil is in fact stored mainly in the reserve cells of the pulp of the pulp, i.e. idioblasts.
  • the avocado kernel is, for its part, poor in oil and is therefore of little interest to the oil mill industry.
  • Outlets have been studied and developed in an attempt to add value to these by-products, which are the skin and the pit: spreading, mulching, horticulture, animal feed, but they do not provide any real added value.
  • constituent parts of the avocado which are the skin and the stone, are naturally low in oil, they contain constituent compounds of the unsaponifiable material having an interesting active potential and high added value.
  • the low content of oil and active compounds in the avocado kernel does not allow the application of a physical treatment by mechanical pressure, this technique not being sufficiently efficient to treat products with oil contents lower than 10%.
  • the co-products of the avocado food industry, and in particular the kernel are poor in oil, but contain all or part of the constituent compounds of the unsaponifiable.
  • the compounds of the alkyl polyols type are constituents of the unsaponifiable material of avocado, and known to be particularly useful in the treatment of connective tissue disorders, such as osteoarthritis.
  • avocado such as avocado pits.
  • the present invention fills this need.
  • the Applicant has thus discovered a new process for obtaining an avocado oil enriched in alkyl polyols or in their acetylated derivatives, in particular from avocado kernel.
  • the method according to the present invention thus makes it possible to enhance the value of the by-products of the avocado, such as the nucleus, and to advantageously extract the compounds present in the nucleus which are not extractable by conventional extraction methods. Such compounds are found solubilized, then extracted by the oil during its extraction within the framework of the process which is the subject of the present invention, and are therefore valued.
  • the process according to the present invention makes it possible, by the use of avocado kernel in a certain proportion, to obtain a certain content of solid particles in the starting product to be extracted, and thus to improve the step of drying the avocado by facilitating the elimination of water.
  • the process which is the subject of the present invention makes it possible to improve, significantly and unexpectedly, the performance of the conventional extraction processes which generally start from avocado pulp, which has been previously removed the core.
  • the use of avocado kernel in a large quantity in the starting product makes it possible to increase the initial dry matter load and thus improve the pressure efficiency of the process by increasing the rate of oil recovered relative to the potential content present in the input material, during the oil extraction step.
  • the increase in the proportion of nucleus allows, by virtue of its mechanical properties, an exchange between the different fractions in contact in the starting material and the extraction of the active compounds, which results in a significant enrichment of the material.
  • the oil extracted mainly from the pulp acts as a vector for dissolving and extracting the specific unsaponifiable compounds contained in the core. Due to their lipophilic nature, these compounds, which are difficult to access within the fibrous structure of the nucleus, are entrained during the pressure extraction step by the flow of oil produced which diffuses throughout the mass brewed in the body of the extraction press.
  • an unsaponifiable from avocado, enriched with alkyl polyols which can be incorporated into cosmetic, dermatological, pharmaceutical or medical device compositions, or even into food compositions, food supplements or nutraceuticals, for human or animal purposes.
  • the present description thus discloses the use of avocado nucleus to obtain an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, said avocado nucleus representing 10 to 50% by mass relative to the total mass. of avocado used.
  • the avocado kernel represents 15 to 40%, typically 20 to 40%, by mass relative to the total mass of avocado used.
  • the present description discloses the use of avocado kernel to obtain, by mechanical pressure, an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, said avocado kernel representing 10 to 50% by mass per relative to the total mass of avocados used, said alkyl polyols being triols of the 1,2,4-trihydroxy type with unbranched C17 to C21 aliphatic chains, saturated, mono or polyunsaturated.
  • avocado pulp is used together with the avocado kernel in the context of the present invention.
  • the avocado pulp represents at least 50% by mass relative to the total mass of avocado used.
  • the present description also discloses the use of the avocado oil contained in the avocado pulp to extract the alkyl polyol compounds and / or their acetylated derivatives from the kernel, the avocado pulp representing at least 50% by mass in relation to the total mass of avocado used.
  • avocado Most varieties of avocado can be used within the scope of the present invention to produce oil, concentrate and then unsaponifiable. avocado, with the desired characteristics, insofar as they contain the qualitative and quantitative potential in specific compounds.
  • the method according to the invention is applied to the most cultivated varieties and representing almost all of the tonnages exported and marketed worldwide, preferably the Hass and Fuerte varieties.
  • the avocados used as the starting product are whole avocados, to which stones can advantageously be added.
  • whole avocados to which stones are added are thus used as the starting mixture.
  • avocados are understood to mean, within the meaning of the present invention, avocados containing the skin, the pulp and the core distributed in their entirety.
  • the avocados used as the starting product are avocados without skin, to which cores can advantageously be added.
  • avocados without skin are thus used, to which stones are added.
  • skinless avocados is meant, within the meaning of the present invention, whole avocados in which the skin has been removed, and thus containing only the core and the pulp.
  • the avocados used as starting product are avocado pulp to which stones are added.
  • the addition of kernel to avocados with or without skin, or to avocado pulp is particularly advantageous, since it thus makes it possible to increase the proportion of kernel relative to the different parts.
  • fruit in the starting mixture used before operating the stages of drying the avocados and extracting the oil This improves the subsequent stages of drying and extraction of oil, especially extraction by mechanical pressure by significantly increasing the pressure efficiency.
  • the joint supply of core in the mass to structure the matrix worked in the extraction press, then of water or water vapor, generates a gas flow and an increase in pressure within the product which promotes the bursting of the cells, the release of the oil, its diffusion in the mass and its expulsion out of the press cage.
  • the avocados used are soft avocados.
  • soft avocados have a degree of softening equivalent to that of immediate consumption of avocado, and preclude pre-treatment by slicing.
  • soft avocados are characterized by the consistency of their flesh measured using a penetrometer and defined by a force of resistance to penetration.
  • the soft avocados have a force of resistance to penetration into the flesh of less than or equal to 3 kg / cm 2 , typically less than or equal to 2 kg / cm 2 , for example less than or equal to 1 kg / cm 2 .
  • the avocados used are not soft avocados. More particularly, according to one embodiment of the invention, the avocados used are hard avocados.
  • hard avocados have a strength of resistance to penetration into the flesh of greater than 3 kg / cm 2 .
  • the penetration force is measured using a penetrometer of the PCE-PTR 200 or FT 327 type, which measures the force in kilograms necessary to make a calibrated tip penetrate into the fruit.
  • the fruit is peeled before taking the measurement in order to overcome the resistance of the skin (integument) and the variability of the different varieties of avocado tested.
  • the rod (point or tip) used for this measurement has a nominal diameter of 6 and 11.3 mm respectively.
  • the avocados used are crushed or sliced, then dried at high temperature, between 60 and 150 ° C, until a residual humidity of less than or equal to 5% is obtained, before obtaining l oil by mechanical pressure.
  • the oil according to the invention is enriched in alkyl polyols and / or in their acetylated derivatives.
  • oil enriched with alkyl polyols and / or their acetylated derivatives is understood to mean an oil containing at least 0.5% by mass of alkyl polyols and / or of their acetylated derivatives. , relative to the total mass of the oil.
  • the oil contains between 0.5 and 10% by mass of alkyl polyols and / or of their acetylated derivatives, for example between 1 and 8%, more particularly between 1.5 and 6%, by mass of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil.
  • the alkyl polyols also called polyhydric fatty alcohols
  • the acetylated derivatives of alkyl polyols are mono-, di, or tri-acetyl compounds, preferably mono-acetylated, typically in position 1, 2 or 4.
  • the avocado oil according to the invention contains sterols and / or saturated aliphatic hydrocarbons.
  • Sterols are in particular tetracyclic hydrocarbons comprising an alcohol function in position 3 and a double bond, the intracyclic position of which is predominantly in position 5.
  • the sterols are advantageously chosen from the group consisting of ⁇ -Sitosterol, Campesterol, Stigmasterol, ⁇ 5-Avenasterol, ⁇ 7-Stigmasterol, Citrostadienol, and mixtures thereof.
  • the oil contains at least 0.5% by mass of sterols, advantageously at least 0.8% by mass of sterols, relative to the total mass of the oil.
  • the saturated aliphatic hydrocarbons are in particular unbranched linear chain hydrocarbons having an odd number of carbons.
  • the saturated aliphatic hydrocarbons are C 27 , C 29 or C 31 alkanes.
  • the saturated aliphatic hydrocarbons according to the invention are chosen from the group consisting of n-heptacosane (CH 3 (CH 2 ) 25 CH 3 ), n-nonacosane (CH 3 (CH 2 ) 27 CH 3 ), n-hentriacontane (CH 3 (CH 2 ) 29 CH 3 ), and mixtures thereof.
  • the oil contains at least 0.01% by mass of saturated aliphatic hydrocarbons, advantageously between 0.01 and 0.10% by mass, relative to the total mass of the oil. .
  • the avocado oil according to the invention contains 1,2-dihydroxy-4-oxo-aliphatic alcohols and / or their acetylated derivatives of “persins” type and / or alkyl furans.
  • 1,2-Dihydroxy-4-oxo-aliphatic alcohols are also called persins, and are precursors of alkyl furans. These are in particular diol ketones of the 1-2-dihydroxy-4-oxo type. with long saturated or acetylenic or olefinic chains. The acetylated derivatives of these compounds are typically in position 1.
  • Persins are typically found in idioblasts, oil cells in the case of avocado.
  • Alkyl furans or aliphatic furans are also called furan lipids or more commonly avocadofurans. They are in particular derivatives of persins comprising a furan group, which result in particular from the chemical transformation by dehydration and intramolecular cyclization of persins extracted from avocado.
  • the avocado oil according to the invention contains at least 2% by mass, more advantageously at least 3% by mass, for example between 3 and 12% by mass of 1,2-dihydroxy-4-oxo-aliphatics alcohols and / or their acetylated derivatives of "persins" type and / or alkyl furans, relative to the total mass of the oil.
  • the alkyl polyols are triols of the 1,2,4-trihydroxy type with unbranched C17 to C21 aliphatic chains, saturated, mono or polyunsaturated, advantageously chosen from the group consisting of nonadecane-1,2 , 4-triol; heneicosa-cis, cis-12-15 diene-1,2,4-triol, heptadec-16-yne-1,2,4-triol; heptadec-cis-16-ene-1,2,4-triol; and their mixtures.
  • the avocados used as the starting product are whole avocados, to which stones can advantageously be added.
  • whole avocados to which stones are added are thus used as the starting mixture.
  • the avocados used as starting product are avocados without skin, to which stones can advantageously be added.
  • avocados without skin are thus used, to which stones are added.
  • Skinless avocados are as defined above.
  • the avocados used as starting product are avocado pulp to which stones are added.
  • the avocados used as starting product have a core content of between 15 and 40% by mass, in particular 20 to 40% by mass, relative to the total mass of avocado used.
  • the grinding (1) is carried out on whole avocados made up of the skin, pulp and kernel, or else on skinless avocados made up of kernel and pulp.
  • Grinding (1) advantageously makes it possible to shred the skin, to fragment the core and to knead the mixture in order to obtain a homogeneous dispersion and particle size of the ground material (particles and pieces obtained) in the avocado pulp.
  • the grinders used adapt to the very large difference in texture and hardness of the different parts that make up the avocado: skin, pulp and kernel.
  • the grinding technology to be used must make it possible to process materials with very hard parts (core) and softer parts (skin), or even very soft (pulp).
  • the grinding (1) is advantageously carried out using a grinder of the type with knives or serrated rollers.
  • the configuration and the setting must, however, be generally adapted as a function of the size of the fruits, their maturity and their quality (biometry between stone, pulp and skin) in order to achieve the advantageously desired particle size.
  • the grinding (1) is carried out in such a way as to obtain a specific size of the particles and pieces, corresponding to a particle size range which gives the ground material a texture suitable for rapid drying.
  • This texture is characterized by a non-continuous visual appearance, the pieces being generally detectable in the mass without the use of a complementary optical instrument.
  • the surface of the ground material is not smooth and has roughness represented by the core and skin particles. During drying, the ground material does not form a compact mass, but easily friable blocks.
  • the grinding (1) leads to obtaining a particle size of the ground material of between 2 and 20 mm, in particular between 2 and 10 mm.
  • the mixture, once crushed, must be distributed in an appropriate manner to guarantee a homogeneity of the drying (2) which follows with the greatest efficiency, advantageously by spreading out in a thin layer, typically to lead to a thin film advantageously between 0.5 and 5 cm, in particular between 1 and 2 cm, or by shaping to optimize the evaporation surface of the extrusion type or passage through a die.
  • the avocados used are tough avocados. Harsh avocados are as defined above.
  • the first step of the process according to the invention consists of slicing the hard avocados.
  • the slicing (1) of avocados is typically done using a disc slicer.
  • the slicing (1) of the avocados advantageously leads to slices with a thickness of 2 to 5 mm.
  • the slices are then distributed evenly on trays or drying racks.
  • the purpose of the following drying step (2) is to extract the water from the medium, but also to make the polar compounds of the unsaponifiable material extractable. It is carried out, in particular, thanks to a specific technology and at a temperature chosen for optimize energy needs and limit unwanted reactions. In fact, too low a temperature would limit the rate of evaporation of the water and would promote the action of lipases, leading to the hydrolysis of glycerides and the increase in the acid number of the medium. Too high a temperature would promote the phenomenon of crusting, as well as thermal and / or oxidative or non-oxidative degradation (Maillard reaction) of the sensitive compounds of the unsaponifiable material or of the unsaturated compounds of the oil.
  • Maillard reaction oxidative or non-oxidative degradation
  • the drying (2) is carried out at a controlled and controlled temperature of between 60 and 150 ° C, in particular between 65 and 120 ° C, for example between 80 and 120 ° C or between 70 and 100 ° C, typically between 80 and 100 ° C.
  • the drying (2) is carried out for 8 to 78 h, advantageously for 10 to 24 h.
  • the drying (2) according to the invention can be carried out in particular by drying under a stream of hot air or under a controlled atmosphere (eg nitrogen), by drying at atmospheric pressure or under vacuum, or by microwave drying.
  • a controlled atmosphere eg nitrogen
  • drying in ventilated dryers in a thin layer and under a current of hot air, at a temperature between 80 and 100 ° C, for 8 to 36 hours is preferred.
  • the dried product has a residual moisture content of less than or equal to 5% m / m.
  • Residual moisture is typically measured using an IR drying thermogravimetric method. Other methods can also be used, such as the oven drying loss method or the Karl Fischer titration method.
  • Residual moisture of 5% or less plays an important role in the consistency of dried avocados, giving them a favorable brittle solid texture. to withstand the physical stresses developed during mechanical pressure. Above 5% moisture, the dried avocado has a soft consistency which, when pressed, leads to the formation of a puree without sufficient consistency to be pressed effectively.
  • This readjustment / addition of water operation (3) must be carried out just before the introduction of the dried fruits into the press by adding purified water or water vapor so that the dry avocados become saturated with moisture without losing their firm consistency and so that no softening appears.
  • the addition of water (3) in the dried avocados is carried out by controlled addition of water or water vapor to the dried avocados, then homogenization by kneading, typically in a planetary mixer, advantageously for 1/2 hour to 1 hour.
  • the addition of water (3) to the dried avocados is carried out continuously in a conveyor of the endless screw type.
  • Water or water vapor is added to the avocados at the head of the conveyor and homogenization is obtained by stirring in the conveyor during the movement of the product.
  • the sizing of the conveyor must typically guarantee a minimum residence time of 1 / 2h for the dried avocados.
  • the conveyor is used to supply the extraction press.
  • the oil extraction step (4) is thus preceded by a step of adding water (3) to the dried avocados by adding 1 to 5%, preferably 1 to 3%, d water or water vapor relative to the mass of dried avocados.
  • the step of adding water (3) to the dried avocados according to the invention is generally preceded by grinding the dried product which homogenizes the feed product.
  • the oil extraction step (4) is carried out by mechanical pressure of the dry matter, advantageously after implementation of the water addition step (3).
  • the extraction presses must receive a material containing a suitable fiber and organic matter content giving the cake produced a certain consistency. This consistency makes it possible to reach, at the head of the press, a high pressure which is essential to guarantee a suitable pressure output.
  • the presence of core particles inside the mixture gives it a consistency and a texture favorable to the extraction of the oil by pressure and thereby improves the productivity and the production of the oil by pressure.
  • the extraction step (4) is carried out at a temperature between 80 and 100 ° C. This temperature is obtained and kept constant by all the means available, such as preheating the body of the press, preheating the dried avocados and then adding water to feed the press, heating the body of the press, etc.
  • maintaining the working temperature of the press at a value greater than 80 ° C, more particularly at 100 ° C, makes it possible to guarantee a good level of oil extraction and to significantly improve the efficiency of the press. extraction of the constituents of the unsaponifiable, in particular the alkyl polyols and / or their acetylated derivatives.
  • the extraction step (4) according to the invention is generally completed by filtration which removes the solid particles and guarantees the clarity of the oil produced.
  • the process according to the present invention thus makes it possible to produce a quality avocado oil with a particular composition, in particular having an index of weak acid and a high potential in unsaponifiable matter and a composition of this particular unsaponifiable matter.
  • a subject of the present invention is thus also an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, capable of being obtained by the process according to the invention.
  • the oil contains at least 0.5% by mass of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil.
  • the oil contains between 0.5 and 10% by mass of alkyl polyols and / or of their acetylated derivatives, for example between 1 and 8%, more particularly between 1.5 and 6%, by mass of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil.
  • alkyl polyols as well as their acetylated derivatives, contained in the oil are as defined above.
  • the avocado oil according to the invention contains sterols and / or saturated aliphatic hydrocarbons.
  • the sterols are advantageously as defined above.
  • the oil contains at least 0.5% by mass of sterols, advantageously at least 0.8% by mass of sterols, relative to the total mass of the oil.
  • saturated aliphatic hydrocarbons are advantageously as defined above.
  • the oil contains at least 0.01% by mass of saturated aliphatic hydrocarbons, advantageously between 0.01 and 0.10% by mass, relative to the total mass of the oil. .
  • the avocado oil according to the invention contains 1,2-dihydroxy-4-oxo-aliphatic alcohols and / or their acetylated derivatives of “persins” type and / or alkyl furans.
  • 1,2-dihydroxy-4-oxo-aliphatic alcohols are advantageously as defined above.
  • the avocado oil according to the invention contains at least 2% by mass, more advantageously at least 3% by mass, for example between 3 and 12% by mass of 1,2-dihydroxy-4-oxo-aliphatics alcohols and / or their acetylated derivatives of "persins" type and / or alkyl furans, relative to the total mass of the oil.
  • the oil according to the invention has a low acid number, generally less than or equal to 5 mg KOH / g, advantageously less than or equal to 4 mg KOH / g, typically less than or equal to 3 mg KOH / g.
  • the present description also discloses a composition containing an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, advantageously at a concentration of between 0.1 and 99.9% by mass, even more advantageously from 30 to 70%. by mass, relative to the total mass of the composition.
  • the present description also discloses the use of avocado oil as defined above for preparing an avocado oil concentrate enriched in alkyl polyols and / or in their acetylated derivatives.
  • avocado oil concentrate enriched in alkyl polyols and / or in their acetylated derivatives is meant within the meaning of the present invention an avocado oil concentrate containing a high content of unsaponifiable, in particular of alkyls. polyols or their derivatives, containing at least 5%, for example between 10 and 30% of alkyl polyols and / or their acetylated derivatives by mass, relative to the total mass of the concentrate.
  • the present description also discloses the use of avocado oil as defined above or of the avocado oil concentrate as mentioned above for preparing an avocado unsaponifiable compound enriched in alkyl polyols.
  • the steps of concentrating the oil in its unsaponifiable fraction to prepare a concentrate as mentioned above, and of preparing an unsaponifiable fraction avocado enriched in alkyl polyols from the oil or from the concentrate are in particular those described below.
  • the preparation of the concentrate is generally carried out by cold crystallization or by molecular distillation.
  • the unsaponifiable concentrate of avocado oil is prepared by molecular distillation, typically at a temperature between 180 and 260 ° C, while maintaining a pressure between 10 -2 and 10 -3 mmHg.
  • This avocado oil molecular distillation step is preferably carried out using a device chosen from centrifugal type molecular stills and scraped film type devices.
  • the preparation of the unsaponifiable avocado enriched in alkyl polyols from the oil or the concentrate generally includes a heat treatment of the oil or the concentrate at a temperature between 80 and 150 ° C, for example between 80 and 130 ° C, followed by a step of saponification and extraction of the unsaponifiable, for example using a solvent.
  • the process for preparing avocado unsaponifiable material enriched in alkyl polyols comprises in particular a step of saponification and extraction of the unsaponifiable material, for example using a solvent.
  • step (5) of saponification and extraction of the unsaponifiable material can be carried out in the presence of potassium hydroxide or sodium hydroxide in an alcoholic medium, preferably ethanolic, followed by one or more extraction (s).
  • Extraction with a suitable organic solvent liquid-liquid extraction
  • the appropriate organic solvent can be, for example chosen from the group of alkanes, halogenated alkanes, aromatic and halogenated aromatic solvents, ethers, ketones, esters, solvents comprising at least one silicon atom, or any other solvent. suitable immiscible with the hydro-alcoholic solution.
  • the present invention also relates to the avocado oil concentrate enriched in unsaponifiable fraction prepared from the avocado oil according to the invention, said concentrate containing at least 5% of alkyl polyols and / or their. acetylated derivatives by mass, relative to the total mass of the concentrate, for its use as a medicament.
  • the present description also discloses the total unsaponifiable matter or the unsaponifiable fraction prepared from the avocado oil according to the invention or from the avocado oil concentrate according to the invention.
  • the present description also discloses an avocado unsaponifiable compound enriched in alkyl polyols, obtainable by the process according to the invention.
  • the avocado unsaponifiable according to the description contains saturated aliphatic hydrocarbons and sterols.
  • the present description also discloses a composition containing an unsaponifiable according to the invention as mentioned above, advantageously at a concentration of between 0.1 and 99.9% by mass, even more advantageously from 30 to 70% by mass, by relative to the total mass of the composition.
  • composition may, in addition, comprise other active ingredients.
  • composition according to the invention contains an avocado unsaponifiable, according to the invention, in combination with a soy unsaponifiable material, advantageously in a ratio of approximately 2/3 for soy and 1/3 for avocado. (such as Piasclédine®300).
  • the composition further comprises at least one compound chosen from the following compounds, known for their properties in the treatment of connective tissue, in particular in the treatment of osteoarthritis: amino sugars such as glucosamine; glucosamine salts, such as glucosamine hydrochloride (for example from 1500 to 2000 mg / d), glucosamine sulfate, glucosamine phosphate and N-acetylglucosamine; glycosaminoglycans (GAGs) such as chondroitin sulfate (for example from 800 to 1200 mg / d); glycosaminoglycan analogs such as polysulfated glycosaminoglycans, or glycosaminoglycan precursors such as hyaluronic acid, glucuronic acid, iduronic acid, keratan sulfate, heparan sulfate, or dermatin sulfate; pentosan or its
  • the composition comprises in combination several of the compounds mentioned above.
  • Glucosamine and chondroitin sulfate are particularly preferred compounds.
  • composition further comprises at least one nonsteroidal anti-inflammatory drug (NSAID), such as paracetamol.
  • NSAID nonsteroidal anti-inflammatory drug
  • the present invention also relates to the unsaponifiable of avocado enriched in alkyl polyols, as described above, for its use as a medicament, for human or animal purposes, advantageously in the prevention and / or treatment of disorders.
  • connective tissue such as osteoarthritis, joint pathologies such as rheumatism, periodontal diseases such as gingivitis or periodontitis.
  • the present invention relates to an unsaponifiable avocado enriched in alkyl polyols, obtainable according to the process of the invention, for its use as a medicament, advantageously in the prevention and / or treatment of disorders of the connective tissue such as osteoarthritis, joint pathologies such as rheumatism, or periodontal diseases, such as gingivitis or periodontitis.
  • compositions as described above for its use as a medicament, for human or animal use, advantageously in the prevention and / or treatment of connective tissue disorders such as osteoarthritis, joint pathologies such as as rheumatism, periodontal diseases, such as gingivitis or periodontitis or in the prevention and / or treatment of disorders of the dermis and / or hypodermis such as skin aging, stretch marks and cellulitis, or else epidermal barrier disorders such as skin inflammation, atopic eczema and irritative and / or inflammatory dermatitis.
  • connective tissue disorders such as osteoarthritis, joint pathologies such as as rheumatism, periodontal diseases, such as gingivitis or periodontitis or in the prevention and / or treatment of disorders of the dermis and / or hypodermis
  • epidermal barrier disorders such as skin inflammation, atopic eczema and irritative and / or inflammatory dermatitis.
  • the unsaponifiable of avocado enriched in alkyl polyols as described above or the composition as described above, for its use.
  • a medical device as a dermatological agent, as a cosmetic agent, or as a nutraceutical, advantageously in the prevention and / or treatment of connective tissue disorders such as osteoarthritis, joint pathologies such as rheumatism, periodontal diseases, such as gingivitis or periodontitis or in the prevention and / or treatment of dermis and / or hypodermis disorders such as skin aging, stretch marks and cellulitis, or even epidermal barrier disorders such as inflammation skin, atopic eczema and irritative and / or inflammatory dermatitis.
  • a medical device is understood to mean any instrument, apparatus, equipment, material, product, with the exception of products of human origin, or other article alone or in combination, intended by the manufacturer for use in the home. man for medical purposes and whose desired main action is not obtained by pharmacological or immunological means or by metabolism, but whose function can be assisted by such means.
  • compositions according to the description are suitable for oral administration, such as a pharmaceutical composition or a drug, a food supplement or a nutraceutical composition.
  • compositions according to the description are suitable for topical administration and include in particular creams, emulsions, milks, ointments, lotions, oils, aqueous or hydro-alcoholic or glycolic solutions, powders, patches, sprays, shampoos, varnishes or any other product for external application.
  • Example 1 Whole avocado including 24.5% kernel
  • the ground material is placed on a 0.158 m 2 tray, to a thickness of 2 cm.
  • the tray is then placed in a ventilated oven and the drying is carried out under air circulation at 80 ⁇ 5 ° C for 24 hours.
  • the dried ground material is recovered and ground for homogenization on the RETSCH type SM 100 cutter mill equipped with a bottom sieve with a 20 mm mesh opening.
  • the water is then added or not to the ground material by spraying a suitable quantity of purified water and the mixture is homogenized in a planetary mixer just before being introduced into the press for extraction of the oil. .
  • the avocado oil is then extracted by mechanical pressure on a laboratory screw press of the Komet type preheated to the determined temperature of the test.
  • Tests n ° 1 and 2 show that the addition of water to the dried fruits before pressing makes it possible to achieve a high pressure yield in the case of test n ° 2, unlike test n ° 1 in which no water addition operation has been implemented.
  • Tests 2 and 3 compared to test 1, demonstrate the cumulative benefit of the temperature and the addition of water to the dry avocados on the pressure yield and on the composition of the oil, in particular on its alkyl polyol content.
  • Example 2 Whole avocado with 25% kernel
  • the tray is then placed in a ventilated oven and the drying is carried out under air circulation at 80 ⁇ 5 ° C for 24 hours.
  • the dried lamellae are collected and crushed for homogenization on the RETSCH type SM 100 knife mill equipped with a bottom sieve with a 20 mm mesh opening.
  • the water is then added or not to the ground material by spraying a suitable quantity of purified water and the mixture is homogenized in a planetary mixer just before being introduced into the press for extraction of the oil. .
  • the avocado oil is then extracted by mechanical pressure on a laboratory screw press of the Komet type preheated to the determined temperature of the test.
  • Tests 4 and 5 demonstrate the cumulative benefit of the temperature and of the addition of water to the dry avocados on the pressure yield and on the composition of the oil, in particular on its alkyl polyol content.
  • 100 kg of fresh pulp, mashed, are spread out on trays in thin layers of a few millimeters and the drying is carried out in a ventilated oven at a temperature of 80 ° C. for 24 hours.
  • the dried product is then ground in a hammer mill.
  • the oil is extracted by mechanical pressure on a laboratory press of the Komet type at a temperature of 100 ° C. and after adding water to the dried avocados by adding 2% water and homogenization.
  • the oil is then filtered through a bell filter under nitrogen pressure and conditioned under a nitrogen atmosphere.
  • Example 3 The operating protocol described in Example 3 was then reproduced in the following examples presented below. The percentages are expressed by mass.
  • Example 6 Whole hard avocados with 11% kernel
  • the average penetration resistance force of avocados is greater than 13 kg / cm 2 .
  • Example 7 Whole hard avocados + kernel (29%)
  • the kernel is present here at a content of 29% by mass in the starting mixture used (whole hard avocados + kernel).
  • the average penetration resistance force of avocados is greater than 13 kg / cm 2 .
  • Example 8 Whole hard avocados + kernel (47%)
  • the stone is present here at a content of 47% by mass in the starting mixture used (whole hard fruits + stone).
  • the average penetration resistance force of avocados is greater than 13 kg / cm 2 .
  • Comparative example 9 Whole soft avocados including kernel (15%)
  • the average penetration resistance force of avocados is less than 2 kg / cm 2 .
  • Test number Material extracted from avocado Content of alkyl polyols and acetylated derivatives Increase compared to pulp alone % m / m % 3 Pulp 1.60 - 4 80% Pulp 1.70 6 20% core 5 60% Pulp 1.86 16 40% core 6 Whole hard avocados including 11% kernel 1.63 2 7 Whole hard avocados with 29% kernel 1.76 10 8 Whole hard avocados including 47% kernel 1.96 22.5 9 Whole soft avocados of which kernel 15% 1.71 7

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Description

La présente description concerne l'utilisation de noyau d'avocat pour obtenir une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés. Avantageusement, ledit noyau d'avocat représente 10 à 50% en masse, en particulier 20 à 40% en masse, par rapport à la masse totale d'avocat utilisé. Les objets de l'invention sont définis dans les revendications. L'invention concerne un procédé d'obtention d'une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés à partir d'au moins des noyaux d'avocats, ladite huile contenant au moins 0,5% en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par rapport à la masse totale de l'huile, lesdits noyaux d'avocat représentant 10 à 50%, en particulier 20 à 40% en masse, par rapport à la masse totale d'avocat utilisé, lesdits avocats utilisés n'étant pas des avocats mous ayant une force de résistance à la pénétration dans la chair inférieure ou égale à 3 kg/cm2, ladite force de résistance étant mesurée à l'aide d'un pénétromètre, tel que défini dans la revendication 1. L'invention concerne également une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, susceptible d'être obtenue par ce procédé, contenant au moins 0,5% en masse d'alkyls polyols ou de leurs dérivés acétylés, par rapport à la masse totale de l'huile. La présente description divulgue également l'utilisation de l'huile d'avocat pour préparer un concentrât d'huile d'avocat enrichi en alkyls polyols et/ou en leurs dérivés acétylés, ou pour préparer un insaponifiable d'avocat enrichi en alkyls polyols. Enfin, l'invention concerne un insaponifiable d'avocat enrichi en alkyls polyols et/ou en leurs dérivés acétylés ou encore un concentrât d'huile d'avocat enrichi en alkyls polyols et/ou en leurs dérivés acétylés, ledit concentrat contenant au moins 5% d'alkyls polyols et/ou de leur dérivés acétylés en masse, par rapport à la masse totale du concentrât, ledit insaponifiable et ledit concentrat d'huile étant susceptible d'être obtenu à partir de ladite huile d'avocat, pour son utilisation comme médicament, avantageusement dans la prévention et/ou le traitement des troubles du tissu conjonctif tels que l'arthrose, des pathologies articulaires telles que les rhumatismes, ou encore des maladies parodontales, telles que la gingivite ou la parodontitc.The present description relates to the use of avocado kernel to obtain an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives. Advantageously, said avocado kernel represents 10 to 50% by mass, in particular 20 to 40% by mass, relative to the total mass of avocado used. The objects of the invention are defined in the claims. The invention relates to a process for obtaining an avocado oil enriched in alkyl polyols and / or their acetylated derivatives from at least avocado pits, said oil containing at least 0.5% by mass. of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil, said avocado nuclei representing 10 to 50%, in particular 20 to 40% by mass, relative to the total mass of 'avocado used, said avocados used not being soft avocados having a resistance force to penetration into the flesh of less than or equal to 3 kg / cm 2 , said resistance force being measured using a penetrometer, as defined in claim 1. The invention also relates to an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, obtainable by this process, containing at least 0.5% by mass of alkyl polyols or their acetylated derivatives, relative to the total mass of the oil. The present description also discloses the use of avocado oil for preparing an avocado oil concentrate enriched in alkyl polyols and / or in their acetylated derivatives, or for preparing an avocado unsaponifiable compound enriched in alkyl polyols. Finally, the invention relates to an avocado unsaponifiable material enriched in alkyl polyols and / or their acetylated derivatives or else an avocado oil concentrate enriched in alkyl polyols and / or their acetylated derivatives, said concentrate containing at least 5 % of alkyl polyols and / or their acetylated derivatives by mass, relative to the total mass of the concentrate, said unsaponifiable and said oil concentrate being obtainable from said avocado oil, for its use as a medicament, advantageously in the prevention and / or treatment of connective tissue disorders such as osteoarthritis, joint pathologies such as rheumatism, or even periodontal diseases, such as gingivitis or periodontitis.

Depuis les années 1990, les débouchés mondiaux de l'avocat se diversifient. Les filières principales restent majoritairement orientées vers l'exportation ou les marchés locaux, en fonction des pays producteurs. Cependant, les volumes destinés à l'industrie sont en forte croissance et sont généralement représentés par la transformation de la pulpe fraîche dans le domaine alimentaire, ainsi que la production d'huile d'avocat de qualité alimentaire ou cosmétique.Since the 1990s, the global market for avocado has diversified. The main sectors remain mainly oriented towards export or local markets, depending on the producing countries. However, volumes intended for industry are growing strongly and are generally represented by the processing of fresh pulp in the food sector, as well as the production of avocado oil of food or cosmetic quality.

Ces dernières applications, si elles restent marginales par rapport aux tonnages dédiés à la commercialisation de l'avocat comme fruit de bouche, permettent de valoriser les écarts de triage et les fruits rejetés par ce marché. Elles représentent une matière première avec un coût d'accès beaucoup plus acceptable.These latter applications, if they remain marginal compared to the tonnages dedicated to the marketing of avocado as a fruit for the palate, make it possible to value the sorting differences and the fruits rejected by this market. They represent a raw material with a much more acceptable cost of access.

Ces industries de transformation sont principalement destinées à la valorisation de la pulpe de l'avocat. Elles génèrent de ce fait des sous-produits, résultant du dépulpage des fruits. A titre d'exemple, les filières de production du guacamole et de l'huile d'avocat alimentaire et cosmétique, obtenue par centrifugation, n'utilisent que la pulpe de l'avocat. Ainsi, sont générées des quantités très importantes de coproduits que sont le noyau et la peau du fruit de l'avocat, qui ne sont pas valorisés dans la filière alimentaire.These processing industries are mainly intended for the valuation of avocado pulp. They therefore generate by-products, resulting from the pulping of the fruits. By way of example, the guacamole and edible and cosmetic avocado oil production channels, obtained by centrifugation, only use avocado pulp. Thus, very large quantities of co-products, which are the stone and the skin of the avocado fruit, are generated, which are not used in the food industry.

L'huile d'avocat est en effet stockée principalement dans les cellules de réserve de la pulpe de la pulpe, i.e. idioblastes. Le noyau de l'avocat est, quant à lui, pauvre en huile et ne présente donc que peu d'intérêt pour la filière des huileries.Avocado oil is in fact stored mainly in the reserve cells of the pulp of the pulp, i.e. idioblasts. The avocado kernel is, for its part, poor in oil and is therefore of little interest to the oil mill industry.

Des débouchés ont été étudiés et développés pour tenter de valoriser ces sous-produits que sont la peau et le noyau : épandage, mulching, horticulture, alimentation animale, mais ils n'apportent pas de réelle valeur ajoutée.Outlets have been studied and developed in an attempt to add value to these by-products, which are the skin and the pit: spreading, mulching, horticulture, animal feed, but they do not provide any real added value.

Cependant, même si les parties constitutives de l'avocat que sont la peau et le noyau sont naturellement pauvres en huile, elles contiennent des composés constitutifs de l'insaponifiable présentant un potentiel actif intéressant et à forte valeur ajoutée.However, even if the constituent parts of the avocado, which are the skin and the stone, are naturally low in oil, they contain constituent compounds of the unsaponifiable material having an interesting active potential and high added value.

Néanmoins, ces composés étant en faibles quantités dans ces parties du fruit, telles que le noyau, elles sont de ce fait difficilement accessibles et extractibles.However, these compounds being in small quantities in these parts of the fruit, such as the stone, they are therefore difficult to access and extract.

La forte teneur en eau des différentes parties constitutives des avocats les rend difficiles à travailler et rend presque impossible leur traitement par les procédés physiques d'extraction connus de l'homme du métier dans des conditions économiques acceptables.The high water content of the various constituent parts of avocados makes them difficult to work with and makes it almost impossible to process them by physical extraction methods known to those skilled in the art under acceptable economic conditions.

Par ailleurs, la faible teneur en huile et en composés actifs dans le noyau d'avocat ne permet pas d'appliquer un traitement physique par pression mécanique, cette technique n'étant pas suffisamment efficace pour traiter des produits présentant des teneurs en huile inférieure à 10%.Furthermore, the low content of oil and active compounds in the avocado kernel does not allow the application of a physical treatment by mechanical pressure, this technique not being sufficiently efficient to treat products with oil contents lower than 10%.

Seule l'extraction par solvant apparaît ainsi comme envisageable, mais outre le fait que ce procédé requiert une technologie complexe, il est réputé pour être onéreux, polluant, à impact pour l'homme et l'environnement.Only solvent extraction thus appears to be possible, but apart from the fact that this process requires complex technology, it is known to be expensive, polluting, with an impact on man and the environment.

Il existait donc un besoin de trouver un procédé qui permette, à faible coût, de valoriser ces composés actifs potentiellement disponibles dans des coproduits facilement accessibles.There was therefore a need to find a process which makes it possible, at low cost, to enhance these potentially available active compounds in easily accessible co-products.

Durant ces dernières décennies, les connaissances de la chimie de l'avocat se sont considérablement enrichies. Plusieurs familles de composés ont ainsi été isolées et identifiées à partir des fruits et de nombreuses études ont été menées pour mettre en évidence leurs activités biologiques. La composition de la fraction insaponifiable de l'huile d'avocat a été particulièrement étudiée.In recent decades, knowledge of avocado chemistry has grown considerably. Several families of compounds have thus been isolated and identified from the fruits and numerous studies have been carried out to demonstrate their biological activities. The composition of the unsaponifiable fraction of avocado oil has been particularly studied.

Les coproduits de l'industrie alimentaire de l'avocat, et notamment le noyau, sont pauvres en huile, mais contiennent tout ou partie des composés constitutifs de l'insaponifiable. En particulier, les composés du type alkyls polyols sont des constituants de l'insaponifiable de l'avocat, et connus pour être particulièrement intéressants dans le traitement de troubles du tissu conjonctif, tels que l'arthrose.The co-products of the avocado food industry, and in particular the kernel, are poor in oil, but contain all or part of the constituent compounds of the unsaponifiable. In particular, the compounds of the alkyl polyols type are constituents of the unsaponifiable material of avocado, and known to be particularly useful in the treatment of connective tissue disorders, such as osteoarthritis.

La demande internationale WO 2013/098393 divulgue un procédé de préparation d'huile d'avocat riche en insaponifiables à partir d'avocats mous entiers, lesdits insaponifiables contenant des acétogénines aliphatiques et/ou leurs dérivés. La demande internationale WO 2013/098393 divulgue ainsi un procédé d'obtention d'une huile d'avocat à partir d'avocats mous entiers, ladite huile contenant au moins 3% en masse insaponifiable par rapport à la masse totale de l'huile, dans laquelle ledit insaponifiable contient des acétogénines aliphatiques et/ou leurs dérivés, comprenant les étapes successives suivantes :

  1. (1) Broyage des avocats mous conduisant à l'obtention d'une granulométrie du broyât comprise entre 2 et 20 mm, en particulier entre 2 et 10 mm,
  2. (2) Séchage du broyât à haute température, avantageusement à une température comprise entre 60 et 150°C, en particulier entre 65 et 120°C, par exemple entre 70 et 100°C, typiquement entre 80 et 100°C, jusqu'à l'obtention d'une humidité résiduelle inférieure ou égale à 5%,
  3. (3) Addition d'eau aux avocats séchés par ajout de 1 à 5 % d'eau ou de vapeur d'eau par rapport à la masse des avocats secs broyés, puis
  4. (4) Extraction de l'huile par pression mécanique.
International demand WO 2013/098393 discloses a process for preparing avocado oil rich in unsaponifiables from whole soft avocados, said unsaponifiables containing aliphatic acetogenins and / or their derivatives. International demand WO 2013/098393 thus discloses a process for obtaining an avocado oil from whole soft avocados, said oil containing at least 3% in unsaponifiable mass relative to the total mass of the oil, in which said unsaponifiable material contains aliphatic acetogenins and / or their derivatives, comprising the following successive steps:
  1. (1) Grinding of the soft avocados leading to obtaining a granulometry of the ground material of between 2 and 20 mm, in particular between 2 and 10 mm,
  2. (2) Drying of the ground material at high temperature, advantageously at a temperature between 60 and 150 ° C, in particular between 65 and 120 ° C, for example between 70 and 100 ° C, typically between 80 and 100 ° C, up to when a residual humidity of 5% or less is obtained,
  3. (3) Addition of water to the dried avocados by adding 1 to 5% water or water vapor relative to the mass of the crushed dry avocados, then
  4. (4) Oil extraction by mechanical pressure.

Par ailleurs, le document BIZIMANA V (« Extraction, characterization, and prediction of the oxidative stability of avocado oil », Dissertation, 1997, pages 1-241, University of Minnesota ) divulgue des méthodes d'extraction d'huile par solvant, tel que l'hexane, l'éthanol ou l'acétone. En particulier, ce document compare deux méthodes d'extraction par solvant (chloroforme/méthanol versus acétone) des tissus d'avocat.Moreover, the document BIZIMANA V (“Extraction, characterization, and prediction of the oxidative stability of avocado oil”, Dissertation, 1997, pages 1-241, University of Minnesota ) discloses methods of extracting oil by solvent, such as hexane, ethanol or acetone. In particular, this document compares two methods of solvent extraction (chloroform / methanol versus acetone) of avocado tissue.

Il était donc intéressant de trouver un procédé qui permette d'extraire à moindre coût certains composés constitutifs de l'insaponifiable d'avocat, tels que mentionnés ci-dessus, en particulier à partir de co-produits ou sous-produits de la filière alimentaire de l'avocat, tels que les noyaux d'avocat.It was therefore interesting to find a process which makes it possible to extract at a lower cost certain constituent compounds of the unsaponifiable of avocado, as mentioned above, in particular from co-products or by-products of the food chain. avocado, such as avocado pits.

La présente invention vient combler ce besoin. La Demanderesse a ainsi découvert un nouveau procédé d'obtention d'une huile d'avocat enrichie en alkyls polyols ou en leurs dérivés acétylés, à partir notamment de noyau d'avocat.The present invention fills this need. The Applicant has thus discovered a new process for obtaining an avocado oil enriched in alkyl polyols or in their acetylated derivatives, in particular from avocado kernel.

Le procédé selon la présente invention permet ainsi de valoriser les sous-produits de l'avocat, tels que le noyau, et d'extraire avantageusement les composés présents dans le noyau qui ne sont pas extractibles par les procédés classiques d'extraction. De tels composés se trouvent solubilisés, puis extraits par l'huile lors de son extraction dans le cadre du procédé objet de la présente invention, et se trouvent de ce fait valorisés.The method according to the present invention thus makes it possible to enhance the value of the by-products of the avocado, such as the nucleus, and to advantageously extract the compounds present in the nucleus which are not extractable by conventional extraction methods. Such compounds are found solubilized, then extracted by the oil during its extraction within the framework of the process which is the subject of the present invention, and are therefore valued.

Par ailleurs, le procédé selon la présente invention permet, de par l'utilisation de noyau d'avocat en une certaine proportion, d'obtenir une certaine teneur en particules solides dans le produit de départ à extraire, et d'améliorer ainsi l'étape de séchage de l'avocat en facilitant l'élimination de l'eau.Moreover, the process according to the present invention makes it possible, by the use of avocado kernel in a certain proportion, to obtain a certain content of solid particles in the starting product to be extracted, and thus to improve the step of drying the avocado by facilitating the elimination of water.

En outre, toujours de par l'utilisation de noyaux d'avocat en une certaine proportion, 10 à 50 % en masse, typiquement 20 à 40 % en masse, par rapport à la masse totale du produit de départ mis en œuvre, avantageusement par l'ajout de noyau aux fruits, le procédé objet de la présente invention permet d'améliorer, de façon significative et inattendue, les performances des procédés classiques d'extraction qui partent généralement de la pulpe d'avocat, dont on a au préalable retiré le noyau. Ainsi, l'utilisation de noyau d'avocat en quantité importante dans le produit de départ permet d'augmenter la charge en matière sèche initiale et ainsi d'améliorer le rendement de pression du procédé en augmentant le taux d'huile récupérée par rapport à la teneur potentielle présente dans la matière entrante, lors de l'étape d'extraction de l'huile.In addition, still by the use of avocado pits in a certain proportion, 10 to 50% by mass, typically 20 to 40% by mass, relative to the total mass of the starting product used, advantageously by the addition of stone to the fruits, the process which is the subject of the present invention makes it possible to improve, significantly and unexpectedly, the performance of the conventional extraction processes which generally start from avocado pulp, which has been previously removed the core. Thus, the use of avocado kernel in a large quantity in the starting product makes it possible to increase the initial dry matter load and thus improve the pressure efficiency of the process by increasing the rate of oil recovered relative to the potential content present in the input material, during the oil extraction step.

Par ailleurs, l'augmentation de la proportion de noyau permet, de par ses propriétés mécaniques, un échange entre les différentes fractions en contact dans la matière de départ et l'extraction des composés actifs, ce qui a pour conséquence un enrichissement notable de l'huile en composés insaponifiables spécifiques, tels que les alkyls polyols et leurs dérivés acétylés.Moreover, the increase in the proportion of nucleus allows, by virtue of its mechanical properties, an exchange between the different fractions in contact in the starting material and the extraction of the active compounds, which results in a significant enrichment of the material. oil in specific unsaponifiable compounds, such as alkyl polyols and their acetylated derivatives.

De façon avantageuse selon la présente invention, l'huile extraite majoritairement de la pulpe joue un rôle de vecteur pour solubiliser et extraire les composés insaponifiables spécifiques contenus dans le noyau. De par leur caractère lipophile, ces composés difficilement accessibles au sein de la structure fibreuse du noyau, se trouvent entrainés lors de l'étape d'extraction par pression par le flux d'huile produite qui diffuse dans toute la masse brassée dans le corps de la presse d'extraction.Advantageously according to the present invention, the oil extracted mainly from the pulp acts as a vector for dissolving and extracting the specific unsaponifiable compounds contained in the core. Due to their lipophilic nature, these compounds, which are difficult to access within the fibrous structure of the nucleus, are entrained during the pressure extraction step by the flow of oil produced which diffuses throughout the mass brewed in the body of the extraction press.

De façon encore plus avantageuse selon l'invention, il a été mis en évidence le rôle favorable de la température sur le taux d'extraction de ces dérivés lors de l'extraction par pression mécanique de l'huile. Les composés alkyls polyols et/ou leurs dérivés acétylés, de par leur structure moléculaire, possèdent un caractère lipophile, mais la présence de fonctions alcools limite leur affinité pour les corps gras, et de ce fait leur solubilité. L'extraction à haute température permet ainsi de réduire l'influence de cette propriété et de garantir un niveau de solubilité suffisant pour obtenir un taux d'extraction performant avec le procédé par pression mécanique.Even more advantageously according to the invention, it has been demonstrated the favorable role of temperature on the rate of extraction of these derivatives during the extraction by mechanical pressure of the oil. Alkyl polyol compounds and / or their acetylated derivatives, by virtue of their molecular structure, have a lipophilic character, but the presence of alcohol functions limits their affinity for fatty substances, and therefore their solubility. Extraction at high temperature thus makes it possible to reduce the influence of this property and to guarantee a sufficient level of solubility to obtain an efficient extraction rate with the process by mechanical pressure.

En outre, on peut avantageusement extraire un insaponifiable d'avocat, enrichi en alkyls polyols, qui peut être incorporé au sein de compositions cosmétiques, dermatologiques, pharmaceutiques ou de dispositifs médicaux, ou encore dans des compositions alimentaires, des compléments alimentaires ou des nutraceutiques, à visée humaine ou animale.In addition, one can advantageously extract an unsaponifiable from avocado, enriched with alkyl polyols, which can be incorporated into cosmetic, dermatological, pharmaceutical or medical device compositions, or even into food compositions, food supplements or nutraceuticals, for human or animal purposes.

La présente description divulgue ainsi l'utilisation de noyau d'avocat pour obtenir une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, ledit noyau d'avocat représentant 10 à 50% en masse par rapport à la masse totale d'avocat utilisé. De manière particulièrement avantageuse, le noyau d'avocat représente 15 à 40%, typiquement 20 à 40%, en masse par rapport à la masse totale d'avocat utilisé.The present description thus discloses the use of avocado nucleus to obtain an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, said avocado nucleus representing 10 to 50% by mass relative to the total mass. of avocado used. In a particularly advantageous manner, the avocado kernel represents 15 to 40%, typically 20 to 40%, by mass relative to the total mass of avocado used.

En particulier, la présente description divulgue l'utilisation de noyau d'avocat pour obtenir par pression mécanique une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, ledit noyau d'avocat représentant 10 à 50% en masse par rapport à la masse totale d'avocats utilisés, lesdits alkyls polyols étant des triols du type 1,2,4-trihydroxy à chaînes aliphatiques non ramifiées en C17 à C21, saturées, mono ou polyinsaturées.In particular, the present description discloses the use of avocado kernel to obtain, by mechanical pressure, an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, said avocado kernel representing 10 to 50% by mass per relative to the total mass of avocados used, said alkyl polyols being triols of the 1,2,4-trihydroxy type with unbranched C17 to C21 aliphatic chains, saturated, mono or polyunsaturated.

De manière particulièrement avantageuse, on utilise de la pulpe d'avocat conjointement au noyau d'avocat dans le cadre de la présente invention. Typiquement, la pulpe de l'avocat représente au moins 50% en masse par rapport à la masse totale d'avocat utilisé.In a particularly advantageous manner, avocado pulp is used together with the avocado kernel in the context of the present invention. Typically, the avocado pulp represents at least 50% by mass relative to the total mass of avocado used.

La présente description divulgue aussi l'utilisation de l'huile d'avocat contenue dans la pulpe de l'avocat pour extraire les composés alkyls polyols et/ou leurs dérivés acétylés du noyau, la pulpe de l'avocat représentant au moins 50% en masse par rapport à la masse totale d'avocat utilisé.The present description also discloses the use of the avocado oil contained in the avocado pulp to extract the alkyl polyol compounds and / or their acetylated derivatives from the kernel, the avocado pulp representing at least 50% by mass in relation to the total mass of avocado used.

La plupart des variétés d'avocat peuvent être utilisées dans le cadre de la présente invention pour produire de l'huile, du concentrat puis l'insaponifiable d'avocat, avec les caractéristiques recherchées, dans la mesure où elles renferment le potentiel qualitatif et quantitatif en composés spécifiques.Most varieties of avocado can be used within the scope of the present invention to produce oil, concentrate and then unsaponifiable. avocado, with the desired characteristics, insofar as they contain the qualitative and quantitative potential in specific compounds.

De manière particulièrement avantageuse, le procédé selon l'invention est appliqué aux variétés les plus cultivées et représentant la quasi totalité des tonnages exportés et commercialisés au niveau mondial, préférentiellement les variétés hass et fuerte. In a particularly advantageous manner, the method according to the invention is applied to the most cultivated varieties and representing almost all of the tonnages exported and marketed worldwide, preferably the Hass and Fuerte varieties.

Dans un mode de réalisation particulier selon la présente invention, les avocats utilisés comme produit de départ sont des avocats entiers, auxquels on peut ajouter avantageusement des noyaux. De manière avantageuse, on utilise ainsi comme mélange de départ des avocats entiers auxquels on ajoute des noyaux.In a particular embodiment according to the present invention, the avocados used as the starting product are whole avocados, to which stones can advantageously be added. Advantageously, whole avocados to which stones are added are thus used as the starting mixture.

Par le terme d'avocats « entiers », on entend, au sens de la présente invention, des avocats contenant la peau, la pulpe et le noyau distribués dans leur intégrité.The term “whole” avocados is understood to mean, within the meaning of the present invention, avocados containing the skin, the pulp and the core distributed in their entirety.

Dans un autre mode de réalisation particulier selon la présente invention, les avocats utilisés comme produit de départ sont des avocats sans peau, auxquels on peut ajouter avantageusement des noyaux. De manière avantageuse, on utilise ainsi comme mélange de départ des avocats sans peau auxquels on ajoute des noyaux.In another particular embodiment according to the present invention, the avocados used as the starting product are avocados without skin, to which cores can advantageously be added. Advantageously, as starting mixture, avocados without skin are thus used, to which stones are added.

Par le terme d'avocats « sans peau », on entend, au sens de la présente invention, des avocats entiers dans lesquels la peau a été retirée, et ne contenant ainsi plus que le noyau et la pulpe.By the term “skinless” avocados is meant, within the meaning of the present invention, whole avocados in which the skin has been removed, and thus containing only the core and the pulp.

Dans un autre mode de réalisation particulier selon la présente invention, les avocats utilisés comme produit de départ sont de la pulpe d'avocat à laquelle on ajoute des noyaux.In another particular embodiment according to the present invention, the avocados used as starting product are avocado pulp to which stones are added.

Dans le cadre de la présente invention, l'ajout de noyau aux avocats avec ou sans peau, ou encore à la pulpe d'avocat, est particulièrement avantageux, puisqu'il permet ainsi d'augmenter la proportion de noyau par rapport aux différentes parties du fruit dans le mélange de départ mis en œuvre avant d'opérer les étapes de séchage des avocats et d'extraction de l'huile. Cela permet d'améliorer les étapes subséquentes de séchage et d'extraction de l'huile, notamment d'extraction par pression mécanique en augmentant significativement le rendement de pression.In the context of the present invention, the addition of kernel to avocados with or without skin, or to avocado pulp, is particularly advantageous, since it thus makes it possible to increase the proportion of kernel relative to the different parts. fruit in the starting mixture used before operating the stages of drying the avocados and extracting the oil. This improves the subsequent stages of drying and extraction of oil, especially extraction by mechanical pressure by significantly increasing the pressure efficiency.

De façon encore plus particulière selon l'invention, il a été montré que l'augmentation de la proportion de noyau par rapport aux différentes parties du fruit dans le mélange de départ devait être accompagnée d'une addition d'eau ou de vapeur d'eau en amont de la pression pour obtenir un rendement de pression optimal.Even more particularly according to the invention, it has been shown that the increase in the proportion of kernel relative to the different parts of the fruit in the starting mixture had to be accompanied by an addition of water or of steam. water upstream of the pressure to obtain optimum pressure efficiency.

Avantageusement selon l'invention, l'apport conjoint de noyau dans la masse pour structurer la matrice travaillée dans la presse d'extraction, puis d'eau ou de vapeur d'eau, génère un flux gazeux et une augmentation de pression au sein du produit qui favorise l'éclatement des cellules, la libération de l'huile, sa diffusion dans la masse et son expulsion hors de la cage de la presse.Advantageously according to the invention, the joint supply of core in the mass to structure the matrix worked in the extraction press, then of water or water vapor, generates a gas flow and an increase in pressure within the product which promotes the bursting of the cells, the release of the oil, its diffusion in the mass and its expulsion out of the press cage.

Selon une caractéristique particulière de la description, les avocats utilisés sont des avocats mous.According to a particular feature of the description, the avocados used are soft avocados.

Typiquement, les avocats mous ont un degré de ramollissement équivalent à celui d'une consommation immédiate de l'avocat, et excluent un prétraitement par tranchage.Typically, soft avocados have a degree of softening equivalent to that of immediate consumption of avocado, and preclude pre-treatment by slicing.

Avantageusement, les avocats mous sont caractérisés par la consistance de leur chair mesurée à l'aide d'un pénétromètre et définie par une force de résistance à la pénétration. De manière particulièrement avantageuse, les avocats mous ont une force de résistance à la pénétration dans la chair inférieure ou égale à 3 kg/cm2, typiquement inférieure ou égale à 2 kg/cm2, par exemple inférieure ou égale à 1 kg/cm2.Advantageously, soft avocados are characterized by the consistency of their flesh measured using a penetrometer and defined by a force of resistance to penetration. In a particularly advantageous manner, the soft avocados have a force of resistance to penetration into the flesh of less than or equal to 3 kg / cm 2 , typically less than or equal to 2 kg / cm 2 , for example less than or equal to 1 kg / cm 2 .

Selon la présente invention, les avocats utilisés ne sont pas des avocats mous. Plus particulièrement, selon un mode de réalisation de l'invention, les avocats utilisés sont des avocats durs.According to the present invention, the avocados used are not soft avocados. More particularly, according to one embodiment of the invention, the avocados used are hard avocados.

Selon la présente invention, les avocats durs ont une force de résistance à la pénétration dans la chair supérieure à 3 kg/cm2.According to the present invention, hard avocados have a strength of resistance to penetration into the flesh of greater than 3 kg / cm 2 .

Typiquement selon la présente invention, la force de pénétration est mesurée à l'aide d'un pénétromètre du type PCE-PTR 200 ou FT 327, qui mesure la force en kilogramme nécessaire pour faire pénétrer un embout calibré dans le fruit. Avantageusement, le fruit est pelé avant de faire la mesure afin de s'affranchir de la résistance de la peau (tégument) et de la variabilité des différentes variétés d'avocat testées. La tige (pointal ou embout) utilisée pour cette mesure a un diamètre nominal respectivement de 6 et de 11,3 mm.Typically according to the present invention, the penetration force is measured using a penetrometer of the PCE-PTR 200 or FT 327 type, which measures the force in kilograms necessary to make a calibrated tip penetrate into the fruit. Advantageously, the fruit is peeled before taking the measurement in order to overcome the resistance of the skin (integument) and the variability of the different varieties of avocado tested. The rod (point or tip) used for this measurement has a nominal diameter of 6 and 11.3 mm respectively.

Selon l'invention, les avocats utilisés sont broyés ou tranchés, puis séchés à haute température, entre 60 et 150°C, jusqu'à l'obtention d'une humidité résiduelle inférieure ou égale à 5%, avant l'obtention de l'huile par pression mécanique.According to the invention, the avocados used are crushed or sliced, then dried at high temperature, between 60 and 150 ° C, until a residual humidity of less than or equal to 5% is obtained, before obtaining l oil by mechanical pressure.

Selon la présente invention, suite au broyage et au séchage des avocats, 1 à 5 % d'eau ou de vapeur d'eau, par rapport à la masse des avocats secs, est additionné avant l'obtention de l'huile par pression mécanique.According to the present invention, following the grinding and drying of the avocados, 1 to 5% of water or water vapor, relative to the mass of the dry avocados, is added before obtaining the oil by mechanical pressure. .

Il a en effet été découvert que lorsque l'on intègre une étape d'injection d'eau ou de vapeur d'eau au sein des avocats séchés, ceci permet d'obtenir une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés avec un rendement élevé.It has in fact been discovered that when a step of injecting water or water vapor into the dried avocados is integrated, this makes it possible to obtain an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives with a high yield.

L'huile selon l'invention est enrichie en alkyls polyols et/ou en leurs dérivés acétylés.The oil according to the invention is enriched in alkyl polyols and / or in their acetylated derivatives.

Par le terme d'huile « enrichie en alkyls polyols et/ou en leurs dérivés acétylés », on entend au sens de la présente invention une huile contenant au moins 0,5% en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par rapport à la masse totale de l'huile. En particulier, l'huile contient entre 0,5 et 10% en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par exemple entre 1 et 8%, plus particulièrement entre 1,5 et 6%, en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par rapport à la masse totale de l'huile.For the purposes of the present invention, the term “oil enriched with alkyl polyols and / or their acetylated derivatives” is understood to mean an oil containing at least 0.5% by mass of alkyl polyols and / or of their acetylated derivatives. , relative to the total mass of the oil. In particular, the oil contains between 0.5 and 10% by mass of alkyl polyols and / or of their acetylated derivatives, for example between 1 and 8%, more particularly between 1.5 and 6%, by mass of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil.

Dans le cadre de l'invention, les alkyls polyols, encore appelés alcools gras polyhydroxylés, sont notamment des triols du type 1,2,4-trihydroxy à chaînes aliphatiques non ramifiées en C17 à C21, saturées, mono ou polyinsaturées, par exemple à longues chaînes acétyléniques et oléfiniques, avantageusement choisis dans le groupe constitué par le nonadecane-1,2,4-triol, le heneicosa-cis, cis-12-15 diene-1,2,4-triol; le heptadec-16-yne-1,2,4-triol, le heptadec-cis-16-ene-1,2,4-triol, et leurs mélanges.In the context of the invention, the alkyl polyols, also called polyhydric fatty alcohols, are in particular triols of the 1,2,4-trihydroxy type with unbranched C17 to C21 aliphatic chains, saturated, mono or polyunsaturated, for example with long acetylenic and olefinic chains, advantageously chosen from the group consisting of nonadecane-1,2,4-triol, heneicosa-cis, cis-12-15 diene-1,2,4-triol; heptadec-16-yne-1,2,4-triol, heptadec-cis-16-ene-1,2,4-triol, and mixtures thereof.

Selon une caractéristique particulière de la présente invention, les dérivés acétylés des alkyls polyols sont des composés mono-, di, ou tri-acétylés, de préférence mono-acétylés, typiquement en position 1, 2 ou 4.According to a particular characteristic of the present invention, the acetylated derivatives of alkyl polyols are mono-, di, or tri-acetyl compounds, preferably mono-acetylated, typically in position 1, 2 or 4.

Typiquement, l'huile d'avocat selon l'invention contient des stérols et/ou des hydrocarbures aliphatiques saturés.Typically, the avocado oil according to the invention contains sterols and / or saturated aliphatic hydrocarbons.

Les stérols sont notamment des hydrocarbures tétracycliques comportant une fonction alcool en position 3 et une double liaison dont la position intracyclique est majoritairement en position 5.Sterols are in particular tetracyclic hydrocarbons comprising an alcohol function in position 3 and a double bond, the intracyclic position of which is predominantly in position 5.

Dans le cadre de l'invention, les stérols sont avantageusement choisis dans le groupe constitué par le β-Sitostérol, le Campestérol, le Stigmastérol, le Δ5-Avenastérol, le Δ7-Stigmastérol, le Citrostadiénol, et leurs mélanges.In the context of the invention, the sterols are advantageously chosen from the group consisting of β-Sitosterol, Campesterol, Stigmasterol, Δ5-Avenasterol, Δ7-Stigmasterol, Citrostadienol, and mixtures thereof.

Selon une caractéristique particulière de l'invention, l'huile contient au moins 0,5% en masse de stérols, avantageusement au moins 0,8% en masse de stérols, par rapport à la masse totale de l'huile.According to a particular characteristic of the invention, the oil contains at least 0.5% by mass of sterols, advantageously at least 0.8% by mass of sterols, relative to the total mass of the oil.

Dans le cadre de l'invention, les hydrocarbures aliphatiques saturés sont notamment des hydrocarbures à chaîne linéaire non ramifiée présentant un nombre impair de carbones. Avantageusement, les hydrocarbures aliphatiques saturés sont des alcanes en C27, C29 ou C31.In the context of the invention, the saturated aliphatic hydrocarbons are in particular unbranched linear chain hydrocarbons having an odd number of carbons. Advantageously, the saturated aliphatic hydrocarbons are C 27 , C 29 or C 31 alkanes.

En particulier, les hydrocarbures aliphatiques saturés selon l'invention sont choisis dans le groupe constitué par le n-heptacosane (CH3(CH2)25CH3), le n-nonacosane (CH3(CH2)27CH3), le n-hentriacontane (CH3(CH2)29CH3), et leurs mélanges.In particular, the saturated aliphatic hydrocarbons according to the invention are chosen from the group consisting of n-heptacosane (CH 3 (CH 2 ) 25 CH 3 ), n-nonacosane (CH 3 (CH 2 ) 27 CH 3 ), n-hentriacontane (CH 3 (CH 2 ) 29 CH 3 ), and mixtures thereof.

Selon une caractéristique particulière de l'invention, l'huile contient au moins 0,01% en masse d'hydrocarbures aliphatiques saturés, avantageusement entre 0,01 et 0,10% en masse, par rapport à la masse totale de l'huile.According to a particular characteristic of the invention, the oil contains at least 0.01% by mass of saturated aliphatic hydrocarbons, advantageously between 0.01 and 0.10% by mass, relative to the total mass of the oil. .

Avantageusement, l'huile d'avocat selon l'invention contient des 1,2-dihydroxy-4-oxo-aliphatiques alcools et/ou leurs dérivés acétylés de type «persins» et/ou des alkyls furanes.Advantageously, the avocado oil according to the invention contains 1,2-dihydroxy-4-oxo-aliphatic alcohols and / or their acetylated derivatives of “persins” type and / or alkyl furans.

Les 1,2-dihydroxy-4-oxo-aliphatiques alcools sont encore appelés persins, et sont des précurseurs des alkyl furanes. Il s'agit notamment des diols cétones du type 1-2-dihydroxy-4-oxo à longues chaînes saturées ou acétyléniques ou oléfiniques. Les dérivés acétylés de ces composés sont typiquement en position 1.1,2-Dihydroxy-4-oxo-aliphatic alcohols are also called persins, and are precursors of alkyl furans. These are in particular diol ketones of the 1-2-dihydroxy-4-oxo type. with long saturated or acetylenic or olefinic chains. The acetylated derivatives of these compounds are typically in position 1.

Les persins se trouvent typiquement dans les idioblastes, cellules oléagineuses dans le cas de l'avocat.Persins are typically found in idioblasts, oil cells in the case of avocado.

Par exemple, on peut citer particulièrement les persins de structure moléculaire suivante :

Figure imgb0001
For example, there may be mentioned in particular persins of the following molecular structure:
Figure imgb0001

Les alkyls furanes ou furanes aliphatiques sont encore appelés lipides furaniques ou plus communément avocadofuranes. Il s'agit notamment de dérivés des persins comportant un groupement furane, qui résultent en particulier de la transformation chimique par déshydratation et cyclisation intramoléculaire des persins extraites de l'avocat. A titre d'exemple, on peut citer les 2-alkyls furanes.Alkyl furans or aliphatic furans are also called furan lipids or more commonly avocadofurans. They are in particular derivatives of persins comprising a furan group, which result in particular from the chemical transformation by dehydration and intramolecular cyclization of persins extracted from avocado. By way of example, mention may be made of 2-alkyl furans.

Avantageusement, l'huile d'avocat selon l'invention contient au moins 2% en masse, plus avantageusement au moins 3% en masse, par exemple entre 3 et 12% en masse de 1,2-dihydroxy-4-oxo-aliphatiques alcools et/ou leurs dérivés acétylés de type «persins» et/ou d'alkyls furanes, par rapport à la masse totale de l'huile.Advantageously, the avocado oil according to the invention contains at least 2% by mass, more advantageously at least 3% by mass, for example between 3 and 12% by mass of 1,2-dihydroxy-4-oxo-aliphatics alcohols and / or their acetylated derivatives of "persins" type and / or alkyl furans, relative to the total mass of the oil.

La présente description divulgue également un procédé d'obtention d'une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, à partir d'au moins des noyaux d'avocats, lesdits noyaux d'avocat représentant 10 à 50% en masse par rapport à la masse totale d'avocats utilisés, comprenant les étapes successives suivantes :

  • Tranchage ou broyage d'avocats contenant une teneur en noyaux de 10 à 50% m/m,
  • Séchage à haute température, avantageusement à une température comprise entre 60 et 150°C, en particulier entre 80 et 120°C, puis
  • Extraction de l'huile.
The present description also discloses a process for obtaining an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, from at least avocado pits, said avocado pits representing 10 to 50 % by mass relative to the total mass of avocados used, comprising the following successive stages:
  • Slicing or crushing avocados with a stone content of 10 to 50% m / m,
  • Drying at high temperature, advantageously at a temperature between 60 and 150 ° C, in particular between 80 and 120 ° C, then
  • Oil extraction.

La présente invention a pour objet un procédé d'obtention d'une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, à partir d'au moins des noyaux d'avocats, ladite huile contenant au moins 0,5% en masse d'alkyls polyols et/ou de leurs dérivés acétylés, lesdits noyaux d'avocat représentant 10 à 50% en masse par rapport à la masse totale d'avocats utilisés, lesdits avocats utilisés n'étant pas des avocats mous ayant une force de résistance à la pénétration dans la chair inférieure ou égale à 3 kg/cm2, ladite force de résistance étant mesurée à l'aide d'un pénétromètre, et ledit procédé comprenant les étapes successives suivantes :

  1. (1) Tranchage ou broyage d'avocats contenant une teneur en noyaux de 10 à 50% m/m, ledit broyage conduisant à l'obtention d'une granulométrie de broyat comprise entre 2 et 20 mm,
  2. (2) Séchage à haute température comprise entre 60 et 150°C, en particulier entre 80 et 120°C, jusqu'à l'obtention d'une humidité résiduelle inférieure ou égale à 5%.
  3. (3) Addition d'eau aux avocats séchés par ajout de 1 à 5% d'eau ou de vapeur d'eau par rapport à la masse des avocats secs, puis avantageusement homogénéisation par malaxage, avant introduction dans la presse, puis
  4. (4) Extraction de l'huile par pression mécanique, avantageusement à une température comprise entre 80 et 100°C.
The present invention relates to a process for obtaining an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, from at least avocado pits, said oil containing at least 0.5 % by mass of alkyl polyols and / or their acetylated derivatives, said avocado cores representing 10 to 50% by mass relative to the total mass of avocados used, said avocados used not being soft avocados having a force of resistance to penetration into the flesh of less than or equal to 3 kg / cm 2 , said resistance force being measured using a penetrometer, and said method comprising the following successive steps:
  1. (1) Slicing or grinding of avocados containing a core content of 10 to 50% m / m, said grinding leading to obtaining a granulometry of ground material of between 2 and 20 mm,
  2. (2) Drying at high temperature between 60 and 150 ° C, in particular between 80 and 120 ° C, until a residual humidity of 5% or less is obtained.
  3. (3) Addition of water to the dried avocados by adding 1 to 5% water or water vapor relative to the mass of the dry avocados, then advantageously homogenization by mixing, before introduction into the press, then
  4. (4) Extraction of the oil by mechanical pressure, advantageously at a temperature between 80 and 100 ° C.

Avantageusement selon la présente invention, les alkyls polyols sont des triols du type 1,2,4-trihydroxy à chaînes aliphatiques non ramifiées en C17 à C21, saturées, mono ou polyinsaturées, avantageusement choisis dans le groupe constitué par le nonadecane-1,2,4-triol; le heneicosa-cis, cis-12-15 diene-1,2,4-triol, le heptadec-16-yne-1,2,4-triol ; le heptadec-cis-16-ene-1,2,4-triol ; et leurs mélanges.Advantageously according to the present invention, the alkyl polyols are triols of the 1,2,4-trihydroxy type with unbranched C17 to C21 aliphatic chains, saturated, mono or polyunsaturated, advantageously chosen from the group consisting of nonadecane-1,2 , 4-triol; heneicosa-cis, cis-12-15 diene-1,2,4-triol, heptadec-16-yne-1,2,4-triol; heptadec-cis-16-ene-1,2,4-triol; and their mixtures.

Dans un mode de réalisation particulier du procédé selon la présente invention, les avocats utilisés comme produit de départ sont des avocats entiers, auxquels on peut ajouter avantageusement des noyaux. De manière avantageuse, on utilise ainsi comme mélange de départ des avocats entiers auxquels on ajoute des noyaux.In a particular embodiment of the process according to the present invention, the avocados used as the starting product are whole avocados, to which stones can advantageously be added. Advantageously, whole avocados to which stones are added are thus used as the starting mixture.

Les avocats entiers sont tels que définis ci-dessus.Whole avocados are as defined above.

Dans un autre mode de réalisation particulier du procédé selon la présente invention, les avocats utilisés comme produit de départ sont des avocats sans peau, auxquels on peut ajouter avantageusement des noyaux. De manière avantageuse, on utilise ainsi comme mélange de départ des avocats sans peau auxquels on ajoute des noyaux.In another particular embodiment of the process according to the present invention, the avocados used as starting product are avocados without skin, to which stones can advantageously be added. Advantageously, as starting mixture, avocados without skin are thus used, to which stones are added.

Les avocats sans peau sont tels que définis ci-dessus.Skinless avocados are as defined above.

Dans un autre mode de réalisation particulier du procédé selon la présente invention, les avocats utilisés comme produit de départ sont de la pulpe d'avocat à laquelle on ajoute des noyaux.In another particular embodiment of the process according to the present invention, the avocados used as starting product are avocado pulp to which stones are added.

Avantageusement selon l'invention, les avocats utilisés comme produit de départ ont une teneur en noyau comprise entre 15 et 40% en masse, en particulier 20 à 40% en masse, par rapport à la masse totale d'avocat utilisé.Advantageously according to the invention, the avocados used as starting product have a core content of between 15 and 40% by mass, in particular 20 to 40% by mass, relative to the total mass of avocado used.

Dans un mode de réalisation particulier selon la présente invention, le broyage (1) est réalisé sur les avocats entiers constitués de la peau, de la pulpe et du noyau, ou encore sur les avocats sans peau constitués du noyau et de la pulpe.In a particular embodiment according to the present invention, the grinding (1) is carried out on whole avocados made up of the skin, pulp and kernel, or else on skinless avocados made up of kernel and pulp.

Le broyage (1) permet avantageusement de déchiqueter la peau, de morceler le noyau et de malaxer le mélange afin d'obtenir une dispersion et une granulométrie homogènes du broyat (particules et morceaux obtenus) dans la pulpe d'avocat.Grinding (1) advantageously makes it possible to shred the skin, to fragment the core and to knead the mixture in order to obtain a homogeneous dispersion and particle size of the ground material (particles and pieces obtained) in the avocado pulp.

Typiquement, les broyeurs utilisés s'adaptent à la très grande différence de texture et de dureté des différentes parties qui composent l'avocat : peau, pulpe et noyau. Ainsi, la technologie de broyeurs à mettre en œuvre doit permettre de traiter des matériaux présentant des parties très dures (noyau) et des parties plus tendres (peau), voire très molles (pulpe).Typically, the grinders used adapt to the very large difference in texture and hardness of the different parts that make up the avocado: skin, pulp and kernel. Thus, the grinding technology to be used must make it possible to process materials with very hard parts (core) and softer parts (skin), or even very soft (pulp).

Le broyage (1) est avantageusement réalisé à l'aide d'un broyeur de type à couteaux ou à rouleaux dentelés.The grinding (1) is advantageously carried out using a grinder of the type with knives or serrated rollers.

La configuration et le réglage doivent cependant être généralement adaptés en fonction de la taille des fruits, de leur maturité et de leur qualité (biométrie entre noyau, pulpe et peau) pour aboutir à la granulométrie avantageusement recherchée.The configuration and the setting must, however, be generally adapted as a function of the size of the fruits, their maturity and their quality (biometry between stone, pulp and skin) in order to achieve the advantageously desired particle size.

Le broyage (1) est réalisé de telle manière à obtenir une taille spécifique des particules et morceaux, répondant à une fourchette de granulométrie qui donne au broyat une texture adaptée à un séchage rapide. Cette texture se caractérise par un aspect visuel non continu, les morceaux étant détectables généralement dans la masse sans utilisation d'un instrument optique complémentaire. Typiquement, la surface du broyat n'est pas lisse et comporte des aspérités représentées par les particules de noyau et de peau. Lors du séchage, le broyat ne forme pas une masse compacte, mais des blocs facilement friables.The grinding (1) is carried out in such a way as to obtain a specific size of the particles and pieces, corresponding to a particle size range which gives the ground material a texture suitable for rapid drying. This texture is characterized by a non-continuous visual appearance, the pieces being generally detectable in the mass without the use of a complementary optical instrument. Typically, the surface of the ground material is not smooth and has roughness represented by the core and skin particles. During drying, the ground material does not form a compact mass, but easily friable blocks.

Selon l'invention, le broyage (1) conduit à l'obtention d'une granulométrie du broyat comprise entre 2 et 20 mm, en particulier entre 2 et 10 mm.According to the invention, the grinding (1) leads to obtaining a particle size of the ground material of between 2 and 20 mm, in particular between 2 and 10 mm.

De manière avantageuse selon l'invention, le mélange, une fois broyé, doit être réparti de façon adaptée pour garantir une homogénéité du séchage (2) qui suit avec la plus grande efficacité, avantageusement par étalement en couche mince, typiquement pour conduire à un film de faible épaisseur avantageusement comprise entre 0,5 et 5 cm, en particulier entre 1 et 2 cm, ou encore par mise en forme permettant d'optimiser la surface d'évaporation du type extrusion ou passage dans une filière.Advantageously according to the invention, the mixture, once crushed, must be distributed in an appropriate manner to guarantee a homogeneity of the drying (2) which follows with the greatest efficiency, advantageously by spreading out in a thin layer, typically to lead to a thin film advantageously between 0.5 and 5 cm, in particular between 1 and 2 cm, or by shaping to optimize the evaporation surface of the extrusion type or passage through a die.

Selon une autre caractéristique de l'invention, les avocats utilisés sont des avocats durs. Les avocats durs sont tels que définis ci-dessus.According to another characteristic of the invention, the avocados used are tough avocados. Harsh avocados are as defined above.

Dans ce cas, la première étape du procédé selon l'invention consiste en un tranchage des avocats durs.In this case, the first step of the process according to the invention consists of slicing the hard avocados.

Le tranchage (1) des avocats est typiquement opéré à l'aide d'une trancheuse à disque.The slicing (1) of avocados is typically done using a disc slicer.

Le tranchage (1) des avocats conduit avantageusement à des tranches d'épaisseur de 2 à 5 mm.The slicing (1) of the avocados advantageously leads to slices with a thickness of 2 to 5 mm.

Les tranches sont ensuite réparties de façon homogène sur des plateaux ou claies de séchage.The slices are then distributed evenly on trays or drying racks.

L'étape suivante de séchage (2) a pour but d'extraire l'eau du milieu, mais aussi de rendre extractibles les composés polaires de l'insaponifiable. Elle est réalisée, en particulier, grâce à une technologie spécifique et à une température choisie pour optimiser les besoins en énergie et limiter les réactions indésirables. En effet, une température trop basse limiterait la vitesse d'évaporation de l'eau et favoriserait l'action des lipases, entraînant l'hydrolyse des glycérides et l'augmentation de l'indice d'acide du milieu. Une température trop élevée favoriserait le phénomène de croûtage, ainsi que la dégradation thermique et/ou oxydative ou non (réaction de Maillard) des composés sensibles de l'insaponifiable ou des composés insaturés de l'huile.The purpose of the following drying step (2) is to extract the water from the medium, but also to make the polar compounds of the unsaponifiable material extractable. It is carried out, in particular, thanks to a specific technology and at a temperature chosen for optimize energy needs and limit unwanted reactions. In fact, too low a temperature would limit the rate of evaporation of the water and would promote the action of lipases, leading to the hydrolysis of glycerides and the increase in the acid number of the medium. Too high a temperature would promote the phenomenon of crusting, as well as thermal and / or oxidative or non-oxidative degradation (Maillard reaction) of the sensitive compounds of the unsaponifiable material or of the unsaturated compounds of the oil.

Il a ainsi été découvert qu'il était recommandé d'utiliser une étape de séchage à température ménagée et contrôlée. La teneur en eau très élevée de l'avocat (≈ 75%) requiert ainsi une technique de séchage très efficace et spécifique pour garantir une évaporation rapide n'induisant pas de dégradation des constituants propres du fruit.It was thus discovered that it was recommended to use a drying step at controlled and controlled temperature. The very high water content of avocado (≈ 75%) thus requires a very efficient and specific drying technique to guarantee rapid evaporation that does not lead to degradation of the specific constituents of the fruit.

Selon l'invention, le séchage (2) est réalisé à température ménagée et contrôlée comprise entre 60 et 150°C, en particulier entre 65 et 120°C, par exemple entre 80 et 120°C ou entre 70 et 100°C, typiquement entre 80 et 100°C.According to the invention, the drying (2) is carried out at a controlled and controlled temperature of between 60 and 150 ° C, in particular between 65 and 120 ° C, for example between 80 and 120 ° C or between 70 and 100 ° C, typically between 80 and 100 ° C.

Selon une caractéristique particulière de l'invention, le séchage (2) est réalisé pendant 8 à 78 h, avantageusement pendant 10 à 24 h.According to a particular characteristic of the invention, the drying (2) is carried out for 8 to 78 h, advantageously for 10 to 24 h.

Le séchage (2) selon l'invention peut être réalisé en particulier par séchage sous courant d'air chaud ou sous atmosphère contrôlée (ex. azote), par séchage à pression atmosphérique ou sous vide, ou par séchage par micro-ondes.The drying (2) according to the invention can be carried out in particular by drying under a stream of hot air or under a controlled atmosphere (eg nitrogen), by drying at atmospheric pressure or under vacuum, or by microwave drying.

Dans le cadre du présent procédé, pour des raisons de facilité de mise en œuvre industrielle et pour des raisons de coût, le séchage en séchoirs ventilés, en couche mince et sous courant d'air chaud, à une température comprise entre 80 et 100°C, pendant 8 à 36 heures est préféré.In the context of the present process, for reasons of ease of industrial implementation and for reasons of cost, drying in ventilated dryers, in a thin layer and under a current of hot air, at a temperature between 80 and 100 ° C, for 8 to 36 hours is preferred.

A l'issue du séchage (2), le produit séché présente un taux d'humidité résiduelle inférieure ou égale à 5% m/m.At the end of the drying (2), the dried product has a residual moisture content of less than or equal to 5% m / m.

L'humidité résiduelle est typiquement mesurée à l'aide d'une méthode thermogravimétrique par séchage IR. D'autres méthodes peuvent également être mises en œuvre, telles que la méthode de perte au séchage en étuve ou la méthode de titrage Karl Fischer.Residual moisture is typically measured using an IR drying thermogravimetric method. Other methods can also be used, such as the oven drying loss method or the Karl Fischer titration method.

Une humidité résiduelle inférieure ou égale à 5% joue un rôle important dans la consistance des avocats séchés, leur conférant une texture solide cassante favorable pour résister aux contraintes physiques développées pendant la pression mécanique. Au-delà de 5% d'humidité, l'avocat séché présente une consistance molle qui conduit, lors de la pression, à la formation d'une purée sans consistance suffisante pour être pressée efficacement.Residual moisture of 5% or less plays an important role in the consistency of dried avocados, giving them a favorable brittle solid texture. to withstand the physical stresses developed during mechanical pressure. Above 5% moisture, the dried avocado has a soft consistency which, when pressed, leads to the formation of a puree without sufficient consistency to be pressed effectively.

Il a été trouvé que, même avec une humidité résiduelle inférieure ou égale à 5 % et une consistance propice à la pression, ces conditions ne sont pas totalement suffisantes pour atteindre des conditions de pression permettant un rendement d'extraction de l'huile élevé.It has been found that, even with a residual humidity of 5% or less and a consistency conducive to pressure, these conditions are not totally sufficient to achieve pressure conditions allowing high oil extraction efficiency.

Il a ainsi été découvert de façon surprenante qu'un réajustement (3) de l'humidité résiduelle par addition de 1 à 5% d'eau ou de vapeur d'eau, par exemple de 1 à 3 % d'eau ou de vapeur d'eau, par rapport à la masse des avocats secs, permettait d'accroitre considérablement le taux d'extraction de l'huile, et de ce fait l'efficacité de la pression.It has thus been surprisingly discovered that a readjustment (3) of the residual humidity by adding 1 to 5% water or water vapor, for example 1 to 3% water or steam of water, relative to the mass of dry avocados, significantly increased the rate of oil extraction, and therefore the effectiveness of the pressure.

Cette opération de réajustement/addition d'eau (3) doit être réalisée juste avant l'introduction des fruits séchés dans la presse par ajout d'eau purifiée ou de vapeur d'eau pour que les avocats secs se saturent en humidité sans perdre leur consistance ferme et afin qu'aucun ramollissement n'apparaisse.This readjustment / addition of water operation (3) must be carried out just before the introduction of the dried fruits into the press by adding purified water or water vapor so that the dry avocados become saturated with moisture without losing their firm consistency and so that no softening appears.

Ce taux d'humidité résiduelle pour être efficace ne peut être obtenu que par déshydratation préalable (2) des avocats, puis réajustement par addition d'eau (3). En effet, une déshydratation partielle contrôlée directe n'aboutit pas à une texture de produit compatible avec la pression, comme il a été signalé précédemment.This residual humidity level to be effective can only be obtained by prior dehydration (2) of the avocados, then readjustment by adding water (3). In fact, a direct controlled partial dehydration does not result in a product texture compatible with the pressure, as has been pointed out previously.

De façon particulière selon l'invention, l'addition d'eau (3) dans les avocats séchés est réalisée par ajout contrôlé d'eau ou de vapeur d'eau sur les avocats séchés, puis homogénéisation par malaxage typiquement dans un mélangeur planétaire, avantageusement pendant 1/2h à 1h.In particular according to the invention, the addition of water (3) in the dried avocados is carried out by controlled addition of water or water vapor to the dried avocados, then homogenization by kneading, typically in a planetary mixer, advantageously for 1/2 hour to 1 hour.

De façon plus particulière selon l'invention, l'addition d'eau (3) dans les avocats séchés est réalisée en continu dans un convoyeur du type vis sans fin. L'eau ou la vapeur d'eau est ajoutée sur les avocats en tête de convoyeur et l'homogénéisation est obtenue par agitation dans le convoyeur, lors du déplacement du produit. Le dimensionnement du convoyeur doit permettre de garantir typiquement un temps de séjour minimum de 1/2h des avocats séchés.More particularly according to the invention, the addition of water (3) to the dried avocados is carried out continuously in a conveyor of the endless screw type. Water or water vapor is added to the avocados at the head of the conveyor and homogenization is obtained by stirring in the conveyor during the movement of the product. The sizing of the conveyor must typically guarantee a minimum residence time of 1 / 2h for the dried avocados.

De façon encore plus particulière selon l'invention, le convoyeur est utilisé pour alimenter la presse d'extraction.Even more particularly according to the invention, the conveyor is used to supply the extraction press.

L'étape d'extraction (4) de l'huile est ainsi précédée d'une étape d'addition d'eau (3) dans les avocats séchés par ajout de 1 à 5%, de préférence de 1 à 3%, d'eau ou de vapeur d'eau par rapport à la masse des avocats séchés.The oil extraction step (4) is thus preceded by a step of adding water (3) to the dried avocados by adding 1 to 5%, preferably 1 to 3%, d water or water vapor relative to the mass of dried avocados.

L'étape d'addition d'eau (3) dans les avocats séchés selon l'invention est généralement précédée par un broyage du produit séché qui homogénéise le produit d'alimentation.The step of adding water (3) to the dried avocados according to the invention is generally preceded by grinding the dried product which homogenizes the feed product.

L'étape d'extraction (4) de l'huile est mise en œuvre par une pression mécanique de la matière sèche, avantageusement après mise œuvre de l'étape d'addition d'eau (3).The oil extraction step (4) is carried out by mechanical pressure of the dry matter, advantageously after implementation of the water addition step (3).

Usuellement, pour pouvoir travailler avec efficacité, les presses d'extraction doivent recevoir une matière contenant une teneur en fibres et matière organique adaptée conférant au tourteau produit une certaine consistance. Cette consistance permet d'atteindre, en tête de presse, une pression élevée indispensable pour garantir un rendement de pression adapté.Usually, in order to be able to work with efficiency, the extraction presses must receive a material containing a suitable fiber and organic matter content giving the cake produced a certain consistency. This consistency makes it possible to reach, at the head of the press, a high pressure which is essential to guarantee a suitable pressure output.

Avantageusement, la présence de particules de noyau à l'intérieur du mélange lui donne une consistance et une texture favorable à l'extraction de l'huile par pression et améliore de ce fait la productivité et la production de l'huile par pression.Advantageously, the presence of core particles inside the mixture gives it a consistency and a texture favorable to the extraction of the oil by pressure and thereby improves the productivity and the production of the oil by pressure.

Avantageusement, l'étape d'extraction (4) est réalisée à une température comprise entre 80 et 100°C. Cette température est obtenue et maintenue constante par tous les moyens à disposition tels que, préchauffage du corps du presse, préchauffage des avocats séchés puis additionnés d'eau en alimentation de la presse, chauffage du corps de presse...Advantageously, the extraction step (4) is carried out at a temperature between 80 and 100 ° C. This temperature is obtained and kept constant by all the means available, such as preheating the body of the press, preheating the dried avocados and then adding water to feed the press, heating the body of the press, etc.

En particulier, le maintien de la température de travail de la presse à une valeur supérieure à 80°C, plus particulièrement à 100°C, permet de garantir un bon niveau d'extraction de l'huile et d'améliorer notablement le rendement d'extraction des constituants de l'insaponifiable, notamment les alkyls polyols et/ou en leurs dérivés acétylés.In particular, maintaining the working temperature of the press at a value greater than 80 ° C, more particularly at 100 ° C, makes it possible to guarantee a good level of oil extraction and to significantly improve the efficiency of the press. extraction of the constituents of the unsaponifiable, in particular the alkyl polyols and / or their acetylated derivatives.

L'étape d'extraction (4) selon l'invention est généralement complétée par une filtration qui élimine les particules solides et garantit la limpidité de l'huile produite.The extraction step (4) according to the invention is generally completed by filtration which removes the solid particles and guarantees the clarity of the oil produced.

Le procédé selon la présente invention permet de produire ainsi une huile d'avocat de qualité avec une composition particulière, notamment possédant un indice d'acide faible et un potentiel élevé en insaponifiable et une composition de cet insaponifiable particulière.The process according to the present invention thus makes it possible to produce a quality avocado oil with a particular composition, in particular having an index of weak acid and a high potential in unsaponifiable matter and a composition of this particular unsaponifiable matter.

La présente invention a ainsi également pour objet une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, susceptible d'être obtenue par le procédé selon l'invention.A subject of the present invention is thus also an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, capable of being obtained by the process according to the invention.

L'huile contient au moins 0,5% en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par rapport à la masse totale de l'huile.The oil contains at least 0.5% by mass of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil.

En particulier, l'huile contient entre 0,5 et 10% en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par exemple entre 1 et 8%, plus particulièrement entre 1,5 et 6%, en masse d'alkyls polyols et/ou de leurs dérivés acétylés, par rapport à la masse totale de l'huile.In particular, the oil contains between 0.5 and 10% by mass of alkyl polyols and / or of their acetylated derivatives, for example between 1 and 8%, more particularly between 1.5 and 6%, by mass of alkyl polyols and / or their acetylated derivatives, relative to the total mass of the oil.

Les alkyls polyols, ainsi que leurs dérivés acétylés, contenus dans l'huile sont tels que définis ci-dessus.The alkyl polyols, as well as their acetylated derivatives, contained in the oil are as defined above.

Typiquement, l'huile d'avocat selon l'invention contient des stérols et/ou des hydrocarbures aliphatiques saturés.Typically, the avocado oil according to the invention contains sterols and / or saturated aliphatic hydrocarbons.

Les stérols sont avantageusement tels que définis ci-dessus.The sterols are advantageously as defined above.

Selon une caractéristique particulière de l'invention, l'huile contient au moins 0,5% en masse de stérols, avantageusement au moins 0,8% en masse de stérols, par rapport à la masse totale de l'huile.According to a particular characteristic of the invention, the oil contains at least 0.5% by mass of sterols, advantageously at least 0.8% by mass of sterols, relative to the total mass of the oil.

Par ailleurs, les hydrocarbures aliphatiques saturés sont avantageusement tels que définis ci-dessus.Furthermore, the saturated aliphatic hydrocarbons are advantageously as defined above.

Selon une caractéristique particulière de l'invention, l'huile contient au moins 0,01% en masse d'hydrocarbures aliphatiques saturés, avantageusement entre 0,01 et 0,10% en masse, par rapport à la masse totale de l'huile.According to a particular characteristic of the invention, the oil contains at least 0.01% by mass of saturated aliphatic hydrocarbons, advantageously between 0.01 and 0.10% by mass, relative to the total mass of the oil. .

Avantageusement, l'huile d'avocat selon l'invention contient des 1,2-dihydroxy-4-oxo-aliphatiques alcools et/ou leurs dérivés acétylés de type «persins» et/ou des alkyls furanes.Advantageously, the avocado oil according to the invention contains 1,2-dihydroxy-4-oxo-aliphatic alcohols and / or their acetylated derivatives of “persins” type and / or alkyl furans.

Les 1,2-dihydroxy-4-oxo-aliphatiques alcools, leurs dérivés acétylés, ainsi que les alkyls furanes, sont avantageusement tels que définis ci-dessus.The 1,2-dihydroxy-4-oxo-aliphatic alcohols, their acetylated derivatives, as well as the alkyl furans, are advantageously as defined above.

Avantageusement, l'huile d'avocat selon l'invention contient au moins 2% en masse, plus avantageusement au moins 3% en masse, par exemple entre 3 et 12% en masse de 1,2-dihydroxy-4-oxo-aliphatiques alcools et/ou leurs dérivés acétylés de type «persins» et/ou d'alkyls furanes, par rapport à la masse totale de l'huile.Advantageously, the avocado oil according to the invention contains at least 2% by mass, more advantageously at least 3% by mass, for example between 3 and 12% by mass of 1,2-dihydroxy-4-oxo-aliphatics alcohols and / or their acetylated derivatives of "persins" type and / or alkyl furans, relative to the total mass of the oil.

De manière particulièrement avantageuse, l'huile selon l'invention présente un faible indice d'acide, généralement inférieur ou égal à 5 mg KOH/g, avantageusement inférieur ou égal à 4 mg KOH/g, typiquement inférieur ou égal à 3 mg KOH/g.Particularly advantageously, the oil according to the invention has a low acid number, generally less than or equal to 5 mg KOH / g, advantageously less than or equal to 4 mg KOH / g, typically less than or equal to 3 mg KOH / g.

La présente description divulgue également une composition contenant une huile d'avocat enrichie en alkyls polyols et/ou en leurs dérivés acétylés, avantageusement à une concentration comprise entre 0,1 et 99,9% en masse, encore plus avantageusement de 30 à 70% en masse, par rapport à la masse totale de la composition.The present description also discloses a composition containing an avocado oil enriched in alkyl polyols and / or in their acetylated derivatives, advantageously at a concentration of between 0.1 and 99.9% by mass, even more advantageously from 30 to 70%. by mass, relative to the total mass of the composition.

La présente description divulgue également l'utilisation de l'huile d'avocat telle que définie ci-dessus pour préparer un concentrat d'huile d'avocat enrichi en alkyls polyols et/ou en leurs dérivés acétylés.The present description also discloses the use of avocado oil as defined above for preparing an avocado oil concentrate enriched in alkyl polyols and / or in their acetylated derivatives.

Par le terme de concentrat d'huile d'avocat enrichi en alkyls polyols et/ou en leurs dérivés acétylés, on entend au sens de la présente invention un concentrat d'huile d'avocat contenant une teneur élevée en insaponifiable, en particulier en alkyls polyols ou en leurs dérivés, contenant au moins 5%, par exemple entre 10 et 30% d'alkyls polyols et/ou de leurs dérivés acétylés en masse, par rapport à la masse totale du concentrat.By the term of avocado oil concentrate enriched in alkyl polyols and / or in their acetylated derivatives, is meant within the meaning of the present invention an avocado oil concentrate containing a high content of unsaponifiable, in particular of alkyls. polyols or their derivatives, containing at least 5%, for example between 10 and 30% of alkyl polyols and / or their acetylated derivatives by mass, relative to the total mass of the concentrate.

La présente description divulgue également l'utilisation de l'huile d'avocat telle que définie ci-dessus ou du concentrat d'huile d'avocat tel que mentionné ci-dessus pour préparer un insaponifiable d'avocat enrichi en alkyls polyols.The present description also discloses the use of avocado oil as defined above or of the avocado oil concentrate as mentioned above for preparing an avocado unsaponifiable compound enriched in alkyl polyols.

Les étapes de concentration de l'huile en sa fraction insaponifiable pour préparer un concentrat tel que mentionné ci-dessus, et de préparation d'un insaponifiable d'avocat enrichi en alkyls polyols à partir de l'huile ou du concentrat sont en particulier celles décrites ci-dessous.The steps of concentrating the oil in its unsaponifiable fraction to prepare a concentrate as mentioned above, and of preparing an unsaponifiable fraction avocado enriched in alkyl polyols from the oil or from the concentrate are in particular those described below.

La préparation du concentrat est généralement opérée par cristallisation à froid ou par distillation moléculaire. Avantageusement, le concentrat en insaponifiable d'huile d'avocat est préparé par distillation moléculaire, typiquement à une température comprise entre 180 et 260°C, en maintenant une pression comprise entre 10-2 et 10-3 mmHg.The preparation of the concentrate is generally carried out by cold crystallization or by molecular distillation. Advantageously, the unsaponifiable concentrate of avocado oil is prepared by molecular distillation, typically at a temperature between 180 and 260 ° C, while maintaining a pressure between 10 -2 and 10 -3 mmHg.

Cette étape de distillation moléculaire de l'huile d'avocat est de préférence réalisée en utilisant un dispositif choisi parmi les distillateurs moléculaires de type centrifuge et les dispositifs de type film raclé.This avocado oil molecular distillation step is preferably carried out using a device chosen from centrifugal type molecular stills and scraped film type devices.

La préparation de l'insaponifiable d'avocat enrichi en alkyls polyols à partir de l'huile ou du concentrat inclut généralement un traitement thermique de l'huile ou du concentrat à une température comprise entre 80 et 150°C, par exemple entre 80 et 130°C, suivie d'une étape de saponification et d'extraction de l'insaponifiable, par exemple à l'aide d'un solvant.The preparation of the unsaponifiable avocado enriched in alkyl polyols from the oil or the concentrate generally includes a heat treatment of the oil or the concentrate at a temperature between 80 and 150 ° C, for example between 80 and 130 ° C, followed by a step of saponification and extraction of the unsaponifiable, for example using a solvent.

Le procédé de préparation de l'insaponifiable d'avocat enrichi en alkyls polyols comprend en particulier une étape de saponification et d'extraction de l'insaponifiable, par exemple à l'aide d'un solvant.The process for preparing avocado unsaponifiable material enriched in alkyl polyols comprises in particular a step of saponification and extraction of the unsaponifiable material, for example using a solvent.

En particulier, l'étape (5) de saponification et d'extraction de l'insaponifiable peut être mise en œuvre en présence de potasse ou de soude en milieu alcoolique, de préférence éthanolique, suivie d'une ou plusieurs extraction(s). L'extraction par un solvant organique approprié (extraction liquide-liquide) en vue de séparer les savons d'acides gras et les composés insaponifiables, est particulièrement adaptée. Le solvant organique approprié peut être, par exemple choisi dans le groupe des alcanes, des alcanes halogénés, des solvants aromatiques et aromatiques halogénés, des éthers, des cétones, des esters, des solvants comprenant au moins un atome de silicium, ou tout autre solvant approprié non miscible avec la solution hydro-alcoolique.In particular, step (5) of saponification and extraction of the unsaponifiable material can be carried out in the presence of potassium hydroxide or sodium hydroxide in an alcoholic medium, preferably ethanolic, followed by one or more extraction (s). Extraction with a suitable organic solvent (liquid-liquid extraction) in order to separate the fatty acid soaps and the unsaponifiable compounds, is particularly suitable. The appropriate organic solvent can be, for example chosen from the group of alkanes, halogenated alkanes, aromatic and halogenated aromatic solvents, ethers, ketones, esters, solvents comprising at least one silicon atom, or any other solvent. suitable immiscible with the hydro-alcoholic solution.

Suite à l'extraction de l'insaponifiable, on peut procéder à des étapes complémentaires de purification ou de fractionnement.Following the extraction of the unsaponifiable, one can proceed to additional stages of purification or fractionation.

La présente invention a également pour objet le concentrat d'huile d'avocat enrichi en fraction insaponifiable préparé à partir de l'huile d'avocat selon l'invention, ledit concentrat contenant au moins 5% d'alkyls polyols et/ou de leurs dérivés acétylés en masse, par rapport à la masse totale du concentrat, pour son utilisation comme médicament.The present invention also relates to the avocado oil concentrate enriched in unsaponifiable fraction prepared from the avocado oil according to the invention, said concentrate containing at least 5% of alkyl polyols and / or their. acetylated derivatives by mass, relative to the total mass of the concentrate, for its use as a medicament.

La présente description divulgue également l'insaponifiable total ou la fraction insaponifiable préparé(e) à partir de l'huile d'avocat selon l'invention ou du concentrat d'huile d'avocat selon l'invention.The present description also discloses the total unsaponifiable matter or the unsaponifiable fraction prepared from the avocado oil according to the invention or from the avocado oil concentrate according to the invention.

La présente description divulgue également un insaponifiable d'avocat enrichi en alkyls polyols, susceptible d'être obtenu par le procédé selon l'invention.The present description also discloses an avocado unsaponifiable compound enriched in alkyl polyols, obtainable by the process according to the invention.

En particulier, l'insaponifiable d'avocat selon la description contient des hydrocarbures aliphatiques saturés et des stérols.In particular, the avocado unsaponifiable according to the description contains saturated aliphatic hydrocarbons and sterols.

La présente description divulgue également une composition contenant un insaponifiable selon l'invention tel que mentionné ci-dessus, avantageusement à une concentration comprise entre 0,1 et 99,9% en masse, encore plus avantageusement de 30 à 70% en masse, par rapport à la masse totale de la composition.The present description also discloses a composition containing an unsaponifiable according to the invention as mentioned above, advantageously at a concentration of between 0.1 and 99.9% by mass, even more advantageously from 30 to 70% by mass, by relative to the total mass of the composition.

Ladite composition peut, en outre, comprendre d'autres actifs.Said composition may, in addition, comprise other active ingredients.

Parmi les actifs recommandés en association avec l'insaponifiable selon l'invention, on peut citer les extraits végétaux, en particulier :

  • Les huiles ou beurres végétaux tels que les huiles de Soja et/ou l'huile de Colza, l'huile de Lupin, avantageusement l'huile de Lupin blanc doux, ou un mélange de ces huiles ou beurres ;
  • l'oléodistillat ou les concentrats d'huile végétale ou animale, notamment de tournesol, plus avantageusement des concentrats de Tournesol linoléiques, tels que l'huile de tournesol concentrée en insaponifiable (Soline®) commercialisée par les Laboratoires Expanscience, les huiles concentrées en insaponifiable du type huile de soja, de colza, de maïs ou de palme ;
  • les insaponifiables de végétaux ou d'huile végétale, avantageusement des furanes d'avocat (Avocadofurane®), les insaponifiables d'Avocat et/ou de Soja, plus particulièrement un mélange d'insaponifiables d'Avocat furaniques et d'insaponifiables de Soja, avantageusement dans un rapport respectif d'environ 1/3-2/3 (tel que Piasclédine®300), les insaponifiables de soja, les insaponifiables stéroliques (typiquement des insaponifiables dont la teneur globale en stérols, en méthylstérols et en alcools triterpèniques, est comprise entre 20 et 95 % en masse, de préférence 45-65 % en masse, par rapport à la masse totale de l'insaponifiable), les phytostérols, les esters de stérols et les dérivés vitaminiques.
Among the active agents recommended in combination with the unsaponifiable according to the invention, mention may be made of plant extracts, in particular:
  • Vegetable oils or butters such as soybean oils and / or rapeseed oil, lupine oil, advantageously mild white lupine oil, or a mixture of these oils or butters;
  • oleodistillate or concentrates of vegetable or animal oil, in particular sunflower oil, more advantageously linoleic sunflower concentrates, such as sunflower oil concentrated in unsaponifiable matter (Soline®) marketed by Laboratoires Expanscience, oils concentrated in unsaponifiable matter of the soybean, colza, corn or palm oil type;
  • plant unsaponifiables or vegetable oil, advantageously avocado furans (Avocadofurane®), avocado and / or soya unsaponifiables, more particularly a mixture of furanic avocado unsaponifiables and soya unsaponifiables, advantageously in a respective ratio of about 1 / 3-2 / 3 (such as Piasclédine®300), soya unsaponifiables, sterolic unsaponifiables (typically unsaponifiables whose overall content of sterols, methylsterols and triterpene alcohols, is between 20 and 95% by mass, preferably 45-65% by mass, relative to the total mass of the unsaponifiable), phytosterols, sterol esters and vitamin derivatives.

En particulier, la composition selon l'invention contient un insaponifiable d'avocat, selon l'invention, en association avec un insaponifiable de soja, avantageusement dans un rapport d'environ 2/3 pour le soja et 1/3 pour l'avocat (tel que Piasclédine®300).In particular, the composition according to the invention contains an avocado unsaponifiable, according to the invention, in combination with a soy unsaponifiable material, advantageously in a ratio of approximately 2/3 for soy and 1/3 for avocado. (such as Piasclédine®300).

Dans un mode de réalisation particulier de la description, la composition comprend en outre au moins un composé choisi parmi les composés suivants, connus pour leurs propriétés dans le traitement du tissu conjonctif, en particulier dans le traitement de l'arthrose :
les sucres aminés tels que la glucosamine ; les sels de glucosamine, tels que le chlorhydrate de glucosamine (par exemple de 1500 à 2000 mg/j), le sulfate de glucosamine, le phosphate de glucosamine et le N-acétylglucosamine ; les glycosaminoglycanes (GAG) tels que la chondroïtine sulfate (par exemple de 800 à 1200 mg/j) ; les analogues de glycosaminoglycanes tels que les glycosaminoglycanes polysulfatés, ou les précurseurs de glycosaminoglycanes tels que l'acide hyaluronique, l'acide glucuronique, l'acide iduronique, le keratane sulfate, le heparane sulfate, ou le dermatine sulfate ; la pentosane ou ses dérivés, en particulier la pentosane sulfate, la pentosane polysulfate (PPS) et les polysaccharides pentosane polysulfates ; la S-adénosylméthionine (SAMe) ; l'adénosine ; la superoxyde dismutase (SOD) ; la L-ergothionine ; les collagènes de type II hydrolysés ou non ; les hydrolysats de collagène tels que la gélatine ; la diacérine ; l'acide arachidonique ; la tétracycline ; les composés analogues de la tétracycline ; la doxycycline ; l'hydroxyproline ; et leurs mélanges.
In a particular embodiment of the description, the composition further comprises at least one compound chosen from the following compounds, known for their properties in the treatment of connective tissue, in particular in the treatment of osteoarthritis:
amino sugars such as glucosamine; glucosamine salts, such as glucosamine hydrochloride (for example from 1500 to 2000 mg / d), glucosamine sulfate, glucosamine phosphate and N-acetylglucosamine; glycosaminoglycans (GAGs) such as chondroitin sulfate (for example from 800 to 1200 mg / d); glycosaminoglycan analogs such as polysulfated glycosaminoglycans, or glycosaminoglycan precursors such as hyaluronic acid, glucuronic acid, iduronic acid, keratan sulfate, heparan sulfate, or dermatin sulfate; pentosan or its derivatives, in particular pentosan sulfate, pentosan polysulfate (PPS) and pentosan polysulfate polysaccharides; S-adenosylmethionine (SAMe); adenosine; superoxide dismutase (SOD); L-ergothionine; type II collagens, hydrolyzed or not; collagen hydrolysates such as gelatin; diacerin; arachidonic acid; tetracycline; tetracycline analog compounds; doxycycline; hydroxyproline; and their mixtures.

Avantageusement, la composition comprend en association plusieurs des composés mentionnés ci-dessus. La glucosamine et la chondroïtine sulfate, seuls ou en association, sont des composés particulièrement préférés.Advantageously, the composition comprises in combination several of the compounds mentioned above. Glucosamine and chondroitin sulfate, alone or in combination, are particularly preferred compounds.

Dans un autre mode de réalisation particulier de la description, la composition comprend en outre au moins un anti-inflammatoire non stéroïdien (AINS), tel que le paracétamol.In another particular embodiment of the description, the composition further comprises at least one nonsteroidal anti-inflammatory drug (NSAID), such as paracetamol.

Enfin, la présente invention a également pour objet l'insaponifiable d'avocat enrichi en alkyls polyols, tel que décrit ci-dessus, pour son utilisation comme médicament, à visée humaine ou animale, avantageusement dans la prévention et/ou le traitement des troubles du tissu conjonctif tels que l'arthrose, des pathologies articulaires telles que les rhumatismes, des maladies parodontales, telles que la gingivite ou la parodontite.Finally, the present invention also relates to the unsaponifiable of avocado enriched in alkyl polyols, as described above, for its use as a medicament, for human or animal purposes, advantageously in the prevention and / or treatment of disorders. connective tissue such as osteoarthritis, joint pathologies such as rheumatism, periodontal diseases such as gingivitis or periodontitis.

En particulier, la présente invention a pour objet un insaponifiable d'avocat enrichi en alkyls polyols, susceptible d'être obtenu selon le procédé de l'invention, pour son utilisation comme médicament, avantageusement dans la prévention et/ou le traitement des troubles du tissu conjonctif tels que l'arthrose, des pathologies articulaires telles que les rhumatismes, ou encore des maladies parodontales, telles que la gingivite ou la parodontite.In particular, the present invention relates to an unsaponifiable avocado enriched in alkyl polyols, obtainable according to the process of the invention, for its use as a medicament, advantageously in the prevention and / or treatment of disorders of the connective tissue such as osteoarthritis, joint pathologies such as rheumatism, or periodontal diseases, such as gingivitis or periodontitis.

La présente description divulgue également la composition telle que décrite ci-dessus, pour son utilisation comme médicament, à visée humaine ou animale, avantageusement dans la prévention et/ou le traitement des troubles du tissu conjonctif tels que l'arthrose, des pathologies articulaires telles que les rhumatismes, des maladies parodontales, telles que la gingivite ou la parodontite ou encore dans la prévention et/ou le traitement des troubles du derme et/ou de l'hypoderme tels que le vieillissement cutané, les vergetures et la cellulite, ou encore des troubles de la barrière épidermique tels que les inflammations cutanées, l'eczéma atopique et les dermatites irritatives et/ou inflammatoires.The present description also discloses the composition as described above, for its use as a medicament, for human or animal use, advantageously in the prevention and / or treatment of connective tissue disorders such as osteoarthritis, joint pathologies such as as rheumatism, periodontal diseases, such as gingivitis or periodontitis or in the prevention and / or treatment of disorders of the dermis and / or hypodermis such as skin aging, stretch marks and cellulitis, or else epidermal barrier disorders such as skin inflammation, atopic eczema and irritative and / or inflammatory dermatitis.

Il est également décrit l'insaponifiable d'avocat enrichi en alkyls polyols, tel que décrit ci-dcssus ou la composition telle que décrite ci-dcssus, pour son utilisation comme dispositif médical, comme agent dermatologique, comme agent cosmétique, ou comme nutraceutique, avantageusement dans la prévention et/ou le traitement des troubles du tissu conjonctif tels que l'arthrose, des pathologies articulaires telles que les rhumatismes, des maladies parodontales, telles que la gingivite ou la parodontite ou encore dans la prévention et/ou le traitement des troubles du derme et/ou de l'hypoderme tels que le vieillissement cutané, les vergetures et la cellulite, ou encore des troubles de la barrière épidermique tels que les inflammations cutanées, l'eczéma atopique et les dermatites irritatives et/ou inflammatoires.It is also described the unsaponifiable of avocado enriched in alkyl polyols, as described above or the composition as described above, for its use. as a medical device, as a dermatological agent, as a cosmetic agent, or as a nutraceutical, advantageously in the prevention and / or treatment of connective tissue disorders such as osteoarthritis, joint pathologies such as rheumatism, periodontal diseases, such as gingivitis or periodontitis or in the prevention and / or treatment of dermis and / or hypodermis disorders such as skin aging, stretch marks and cellulitis, or even epidermal barrier disorders such as inflammation skin, atopic eczema and irritative and / or inflammatory dermatitis.

Par ailleurs, on entend par dispositif médical selon la description tout instrument, appareil, équipement, matière, produit, à l'exception des produits d'origine humaine, ou autre article seul ou en association, destiné par le fabricant à être utilisé chez l'homme à des fins médicales et dont l'action principale voulue n'est pas obtenue par des moyens pharmacologiques ou immunologiques ni par métabolisme, mais dont la fonction peut être assistée par de tels moyens.Furthermore, according to the description, a medical device is understood to mean any instrument, apparatus, equipment, material, product, with the exception of products of human origin, or other article alone or in combination, intended by the manufacturer for use in the home. man for medical purposes and whose desired main action is not obtained by pharmacological or immunological means or by metabolism, but whose function can be assisted by such means.

Avantageusement, les compositions selon la description sont adaptées à une administration orale, telles qu'une composition pharmaceutique ou un médicament, un complément alimentaire ou une composition nutraceutique.Advantageously, the compositions according to the description are suitable for oral administration, such as a pharmaceutical composition or a drug, a food supplement or a nutraceutical composition.

Selon une variante, les compositions selon la description sont adaptées à l'administration topique et incluent notamment les crèmes, les émulsions, les laits, les pommades, les lotions, les huiles, les solutions aqueuses ou hydro-alcooliques ou glycoliques, les poudres, les patchs, les sprays, les shampooings, les vernis ou tout autre produit pour application externe.According to one variant, the compositions according to the description are suitable for topical administration and include in particular creams, emulsions, milks, ointments, lotions, oils, aqueous or hydro-alcoholic or glycolic solutions, powders, patches, sprays, shampoos, varnishes or any other product for external application.

Les exemples suivants sont donnés pour illustrer l'invention :The following examples are given to illustrate the invention:

Exemple 1: Avocat entier dont noyau 24,5%Example 1: Whole avocado including 24.5% kernel

3 kg d'avocats d'origine kényane, de calibre 18, de variété hass et de dureté mesurée à l'aide d'un pénétromètre, supérieure à 13 Kg/cm2 et dont la part de noyaux représente 24,5% en masse, sont broyés dans un broyeur à couteaux RETSCH du type SM 100 équipé selon la granulométrie souhaitée de tamis de fond à ouverture de maille de 10 mm.3 kg of avocados of Kenyan origin, size 18, Hass variety and hardness measured using a penetrometer, greater than 13 Kg / cm 2 and whose share of kernels represents 24.5% by mass , are ground in a RETSCH cutter mill of the type SM 100 equipped according to the desired particle size with a bottom sieve with a mesh size of 10 mm.

Le broyat est déposé sur un plateau de 0,158 m2, sur une épaisseur de 2 cm.The ground material is placed on a 0.158 m 2 tray, to a thickness of 2 cm.

Le plateau est ensuite disposé dans une étuve ventilée et le séchage est réalisé sous une circulation d'air à 80 ± 5 °C pendant 24 heures.The tray is then placed in a ventilated oven and the drying is carried out under air circulation at 80 ± 5 ° C for 24 hours.

Le broyat séché est récupéré et broyé pour homogénéisation sur le broyeur à couteaux RETSCH du type SM 100 équipé de tamis de fond à ouverture de maille de 20 mm.The dried ground material is recovered and ground for homogenization on the RETSCH type SM 100 cutter mill equipped with a bottom sieve with a 20 mm mesh opening.

Suivant les essais, l'eau est ensuite ajoutée ou non sur le broyat par vaporisation d'une quantité d'eau purifiée adaptée et le mélange est homogénéisé dans un mélangeur planétaire juste avant d'être introduit dans la presse pour extraction de l'huile.Depending on the tests, the water is then added or not to the ground material by spraying a suitable quantity of purified water and the mixture is homogenized in a planetary mixer just before being introduced into the press for extraction of the oil. .

L'huile d'avocat est ensuite extraite par pression mécanique sur une presse à vis de laboratoire du type Komet préchauffée à la température déterminée de l'essai.The avocado oil is then extracted by mechanical pressure on a laboratory screw press of the Komet type preheated to the determined temperature of the test.

Les quantités d'huile et de tourteau sont déterminées par pesée pour chaque essai et le rendement d'extraction est calculé par la formule suivante : Masse d'huile récupérée × 100 / Masse d'huile récupérée + masse de tourteau .

Figure imgb0002
The quantities of oil and cake are determined by weighing for each test and the extraction yield is calculated by the following formula: Mass oil recovered × 100 / Mass oil recovered + mass of cake .
Figure imgb0002

L'analyse physico-chimique et chromatographique des huiles permet de comparer les compositions des différentes huiles obtenues. N° essai % eau ajoutée après séchage Température de pression Rendement d'extraction Teneur en alkyls polyols % °C % m/m 1 0 80 15.2 2.44 2 3 80 40.0 2.52 3 3 100 40.4 3.01 The physico-chemical and chromatographic analysis of the oils makes it possible to compare the compositions of the different oils obtained. Test number % water added after drying Pressure temperature Extraction efficiency Alkyl polyol content % ° C % m / m 1 0 80 15.2 2.44 2 3 80 40.0 2.52 3 3 100 40.4 3.01

Les essais n°1 et 2 mettent en évidence que l'addition d'eau aux fruits séchés avant pression permet d'atteindre un rendement de pression élevé dans le cas de l'essai n°2, contrairement à l'essai n°1 dans lequel aucune opération d'addition d'eau n'a été mise en œuvre.Tests n ° 1 and 2 show that the addition of water to the dried fruits before pressing makes it possible to achieve a high pressure yield in the case of test n ° 2, unlike test n ° 1 in which no water addition operation has been implemented.

Les essais 2 et 3, comparativement à l'essai 1, mettent en évidence le bénéfice cumulé de la température et de l'addition d'eau aux avocats secs sur le rendement de pression et sur la composition de l'huile, notamment sur sa teneur en alkyls polyols.Tests 2 and 3, compared to test 1, demonstrate the cumulative benefit of the temperature and the addition of water to the dry avocados on the pressure yield and on the composition of the oil, in particular on its alkyl polyol content.

Exemple 2: Avocat entier dont noyau 25%Example 2: Whole avocado with 25% kernel

3 kg d'avocats d'origine kényane, de calibre 18, de variété hass et de dureté mesurée à l'aide d'un pénétromètre, supérieure à 13 Kg/cm2 et dont la part de noyaux représente 25% en masse, sont tranchés en lamelles de 2 à 5 mm, puis répartis en couches régulières sur des plateaux.3 kg of avocados of Kenyan origin, size 18, Hass variety and hardness measured using a penetrometer, greater than 13 Kg / cm 2 and whose share of pits represents 25% by mass, are Sliced into 2 to 5 mm strips, then distributed in regular layers on trays.

Le plateau est ensuite disposé dans une étuve ventilée et le séchage est réalisé sous une circulation d'air à 80 ± 5 °C pendant 24 heures.The tray is then placed in a ventilated oven and the drying is carried out under air circulation at 80 ± 5 ° C for 24 hours.

Les lamelles séchées est récupérées et broyées pour homogénéisation sur le broyeur à couteaux RETSCH du type SM 100 équipé de tamis de fond à ouverture de maille de 20 mm.The dried lamellae are collected and crushed for homogenization on the RETSCH type SM 100 knife mill equipped with a bottom sieve with a 20 mm mesh opening.

Suivant les essais, l'eau est ensuite ajoutée ou non sur le broyat par vaporisation d'une quantité d'eau purifiée adaptée et le mélange est homogénéisé dans un mélangeur planétaire juste avant d'être introduit dans la presse pour extraction de l'huile.Depending on the tests, the water is then added or not to the ground material by spraying a suitable quantity of purified water and the mixture is homogenized in a planetary mixer just before being introduced into the press for extraction of the oil. .

L'huile d'avocat est ensuite extraite par pression mécanique sur une presse à vis de laboratoire du type Komet préchauffée à la température déterminée de l'essai.The avocado oil is then extracted by mechanical pressure on a laboratory screw press of the Komet type preheated to the determined temperature of the test.

Les quantités d'huile et de tourteau sont déterminées par pesée pour chaque essai et le rendement d'extraction est calculé par la formule suivante : Masse d'huile récupérée × 100 / Masse d'huile récupérée + masse de tourteau .

Figure imgb0003
The quantities of oil and cake are determined by weighing for each test and the extraction yield is calculated by the following formula: Mass oil recovered × 100 / Mass oil recovered + mass of cake .
Figure imgb0003

L'analyse physico-chimique et chromatographique des huiles permet de comparer les compositions des différentes huiles obtenues. N° essai % eau ajoutée après séchage Température de pression Rendement d'extraction Teneur en alkyls polyols % °C % m/m 4 0 80 28,8 3,02 5 3 100 40.8 3.19 The physico-chemical and chromatographic analysis of the oils makes it possible to compare the compositions of the different oils obtained. Test number % water added after drying Pressure temperature Extraction efficiency Alkyl polyol content % ° C % m / m 4 0 80 28.8 3.02 5 3 100 40.8 3.19

Les essais 4 et 5 mettent en évidence le bénéfice cumulé de la température et de l'addition d'eau aux avocats secs sur le rendement de pression et sur la composition de l'huile, notamment sur sa teneur en alkyls polyols.Tests 4 and 5 demonstrate the cumulative benefit of the temperature and of the addition of water to the dry avocados on the pressure yield and on the composition of the oil, in particular on its alkyl polyol content.

Exemple 3 comparatif : pulpe seuleComparative Example 3: pulp alone

100 kg de pulpe fraîche, mise en purée, sont étalés sur des plateaux en fines couches de quelques millimètres et le séchage est opéré en étuve ventilée à une température de 80°C pendant 24 heures. Le produit séché est ensuite broyé dans un broyeur à marteaux.100 kg of fresh pulp, mashed, are spread out on trays in thin layers of a few millimeters and the drying is carried out in a ventilated oven at a temperature of 80 ° C. for 24 hours. The dried product is then ground in a hammer mill.

29,5 kg de pulpe sèche sont récupérés représentant une perte au séchage de 70,5%.29.5 kg of dry pulp are recovered, representing a loss on drying of 70.5%.

L'huile est extraite par pression mécanique sur une presse de laboratoire du type Komet à une température de 100°C et après addition d'eau aux avocats séchés par ajout de 2% d'eau et homogénéisation. L'huile est ensuite filtrée sur filtre cloche sous pression d'azote et conditionnée sous atmosphère d'azote.The oil is extracted by mechanical pressure on a laboratory press of the Komet type at a temperature of 100 ° C. and after adding water to the dried avocados by adding 2% water and homogenization. The oil is then filtered through a bell filter under nitrogen pressure and conditioned under a nitrogen atmosphere.

Les analyses chromatographiques de l'huile ont donné les résultats suivants (% en masse) :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes : 4,63% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,60% ;
  • Teneur en stérols : 0,58% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,01%.
Chromatographic analyzes of the oil gave the following results (% by mass):
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 4.63%;
  • Content of alkyl polyols and their acetylated derivatives: 1.60%;
  • Sterol content: 0.58%;
  • Content of saturated aliphatic hydrocarbons: 0.01%.

Le protocole opératoire décrit dans l'exemple 3 a été reproduit ensuite dans les exemples suivants présentés ci-dessous. Les pourcentages sont exprimés en masse.The operating protocol described in Example 3 was then reproduced in the following examples presented below. The percentages are expressed by mass.

Exemple 4 : mélange pulpe + noyau 20%Example 4: pulp + kernel mixture 20%

80 kg de pulpe fraiche, sont broyés avec 20 kg de noyaux, puis étalés sur des plateaux en un film mince de quelques millimètres d'épaisseur.80 kg of fresh pulp, are crushed with 20 kg of stones, then spread on trays in a thin film a few millimeters thick.

33,5 kg de produit sec sont récupérés représentant une perte au séchage de 66,5%.33.5 kg of dry product are recovered, representing a loss on drying of 66.5%.

Les analyses chromatographiques de l'huile ont donné les résultats suivants :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes: 4,78% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,70% ;
  • Teneur en stérols : 0,60% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,01%.
Chromatographic analyzes of the oil gave the following results:
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 4.78%;
  • Content of alkyl polyols and their acetylated derivatives: 1.70%;
  • Sterol content: 0.60%;
  • Content of saturated aliphatic hydrocarbons: 0.01%.

L'utilisation de 20% de noyau dans le mélange avocat mis en œuvre permet d'augmenter de 6% la teneur en alkyls polyols et leurs dérivés acétylés par rapport à l'huile obtenue à partir de pulpe seule (exemple 3).The use of 20% of core in the avocado mixture used makes it possible to increase the content of alkyl polyols and their acetylated derivatives by 6% relative to the oil obtained from the pulp alone (example 3).

Exemple 5 : mélange pulpe + noyau 40%Example 5: pulp + kernel mixture 40%

60 kg de pulpe fraiche, sont broyés avec 40 kg de noyaux, puis étalés sur des plateaux en un film mince de quelques millimètres d'épaisseur.60 kg of fresh pulp, are crushed with 40 kg of stones, then spread on trays in a thin film a few millimeters thick.

37,5 kg de produit sec sont récupérés représentant une perte au séchage de 62,5%.37.5 kg of dry product are recovered, representing a loss on drying of 62.5%.

Les analyses chromatographiques de l'huile ont donné les résultats suivants :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes : 5,00% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,86% ;
  • Teneur en stérols : 0,62% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,01%.
Chromatographic analyzes of the oil gave the following results:
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 5.00%;
  • Content of alkyl polyols and their acetylated derivatives: 1.86%;
  • Sterol content: 0.62%;
  • Content of saturated aliphatic hydrocarbons: 0.01%.

L'utilisation de 40% de noyau dans le mélange avocat mis en œuvre permet d'augmenter de 16% la teneur en alkyls polyols et leurs dérivés acétylés par rapport à l'huile obtenue à partir de pulpe seule (exemple 3).The use of 40% of core in the avocado mixture used makes it possible to increase the content of alkyl polyols and their acetylated derivatives by 16% relative to the oil obtained from the pulp alone (example 3).

Exemple 6 : Avocats durs entiers dont noyau 11%Example 6: Whole hard avocados with 11% kernel

La force de résistance à la pénétration moyenne des avocats est supérieure à 13 kg/cm2.The average penetration resistance force of avocados is greater than 13 kg / cm 2 .

100 kg d'avocats entiers frais sont tranchés en lamelles de 2 à 5 mm puis répartis en couches régulières sur des plateaux.100 kg of fresh whole avocados are sliced into 2 to 5 mm strips then distributed in regular layers on trays.

31,2 kg d'avocats séchés sont récupérés représentant une perte au séchage de 68,8 %.31.2 kg of dried avocados are recovered, representing a loss on drying of 68.8%.

Les analyses chromatographiques de l'huile ont donné les résultats suivants :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes : 4,63% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,63% ;
  • Teneur en stérols : 0,61% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,04%.
Chromatographic analyzes of the oil gave the following results:
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 4.63%;
  • Content of alkyl polyols and their acetylated derivatives: 1.63%;
  • Sterol content: 0.61%;
  • Content of saturated aliphatic hydrocarbons: 0.04%.

L'utilisation de 11% de noyau dans le mélange avocat mis en œuvre permet d'augmenter de 2% la teneur en alkyls polyols et leurs dérivés acétylés par rapport à l'huile obtenue à partir de pulpe seule (exemple 3).The use of 11% of core in the avocado mixture used makes it possible to increase the content of alkyl polyols and their acetylated derivatives by 2% relative to the oil obtained from the pulp alone (example 3).

Exemple 7 : Avocats durs entiers + noyau (29%)Example 7: Whole hard avocados + kernel (29%)

Le noyau est présente ici à une teneur de 29% en masse dans le mélange de départ mis en œuvre (Avocats durs entiers + noyau).The kernel is present here at a content of 29% by mass in the starting mixture used (whole hard avocados + kernel).

La force de résistance à la pénétration moyenne des avocats est supérieure à 13 kg/cm2.The average penetration resistance force of avocados is greater than 13 kg / cm 2 .

80 kg d'avocat durs entiers frais auxquels sont ajoutés 20 kg de noyaux humides sont tranchés en lamelles de 2 à 5 mm puis répartis en couches régulières sur des plateaux.80 kg of fresh whole hard avocado to which are added 20 kg of wet pits are sliced into 2 to 5 mm strips then distributed in regular layers on trays.

34,8 kg d'avocats séchés sont récupérés représentant une perte au séchage de 65,2 %.34.8 kg of dried avocados are recovered, representing a loss on drying of 65.2%.

Les analyses chromatographiques de l'huile ont donné les résultats suivants :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes : 4,81% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,76% ;
  • Teneur en stérols : 0,63% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,04%.
Chromatographic analyzes of the oil gave the following results:
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 4.81%;
  • Content of alkyl polyols and their acetylated derivatives: 1.76%;
  • Sterol content: 0.63%;
  • Content of saturated aliphatic hydrocarbons: 0.04%.

L'utilisation de 29% de noyau dans le mélange avocat mis en œuvre permet d'augmenter de 10% la teneur en alkyls polyols et leurs dérivés acétylés par rapport à l'huile obtenue à partir de pulpe seule (exemple 3).The use of 29% of core in the avocado mixture used makes it possible to increase the content of alkyl polyols and their acetylated derivatives by 10% relative to the oil obtained from the pulp alone (example 3).

Exemple 8 : Avocats durs entiers + noyau (47%)Example 8: Whole hard avocados + kernel (47%)

Le noyau est présente ici à une teneur de 47% en masse dans le mélange de départ mis en œuvre (fruits durs entiers + noyau).The stone is present here at a content of 47% by mass in the starting mixture used (whole hard fruits + stone).

La force de résistance à la pénétration moyenne des avocats est supérieure à 13 kg/cm2.The average penetration resistance force of avocados is greater than 13 kg / cm 2 .

60 kg d'avocats entiers frais auxquels sont ajoutés 40 kg de noyaux humides sont tranchés en lamelles de 2 à 5 mm puis répartis en couches régulières sur des plateaux.60 kg of fresh whole avocados to which are added 40 kg of wet pits are sliced into 2 to 5 mm strips then distributed in regular layers on trays.

38,5 kg d'avocats séchés sont récupérés représentant une perte au séchage de 61,5 %.38.5 kg of dried avocados are recovered, representing a loss on drying of 61.5%.

Les analyses chromatographiques de l'huile ont donné les résultats suivants :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes : 5,10% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,96% ;
  • Teneur en stérols : 0,66% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,04%.
Chromatographic analyzes of the oil gave the following results:
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 5.10%;
  • Content of alkyl polyols and their acetylated derivatives: 1.96%;
  • Sterol content: 0.66%;
  • Content of saturated aliphatic hydrocarbons: 0.04%.

L'utilisation de 47% de noyau dans le mélange avocat mis en œuvre permet d'augmenter de 22,5% la teneur en alkyls polyols et leurs dérivés acétylés par rapport à l'huile obtenue à partir de pulpe seule (exemple 3)The use of 47% of core in the avocado mixture used makes it possible to increase the content of alkyl polyols and their acetylated derivatives by 22.5% relative to the oil obtained from the pulp alone (example 3)

Exemple 9 comparatif : Avocats mous entiers dont noyau (15%)Comparative example 9: Whole soft avocados including kernel (15%)

La force de résistance à la pénétration moyenne des avocats est inférieure à 2 kg/cm2.The average penetration resistance force of avocados is less than 2 kg / cm 2 .

100 kg d'avocat mous entiers sont broyés dans un broyeur à couteaux, puis étalés sur des plateaux en un film mince de quelques millimètres d'épaisseur.100 kg of whole soft avocado are crushed in a knife mill, then spread on trays in a thin film a few millimeters thick.

35,2 kg d'avocats séchés sont récupérés représentant une perte au séchage de 64,8 %.35.2 kg of dried avocados are recovered, representing a loss on drying of 64.8%.

Les analyses chromatographiques de l'huile ont donné les résultats suivants :

  • Teneur en 1,2-dihydroxy-4-oxo-aliphatiques alcools et leurs dérivés acétylés de type «persins» et alkyls furanes : 3,58% ;
  • Teneur en alkyls polyols et leurs dérivés acétylés : 1,71% ;
  • Teneur en stérols : 0,66% ;
  • Teneur en hydrocarbures aliphatiques saturés : 0,03%.
Chromatographic analyzes of the oil gave the following results:
  • Content of 1,2-dihydroxy-4-oxo-aliphatic alcohols and their acetylated derivatives of “persins” type and alkyl furans: 3.58%;
  • Content of alkyl polyols and their acetylated derivatives: 1.71%;
  • Sterol content: 0.66%;
  • Content of saturated aliphatic hydrocarbons: 0.03%.

L'utilisation de 15% de noyau dans le mélange avocat mis en œuvre permet d'augmenter de 7% la teneur en alkyls polyols et leurs dérivés acétylés par rapport à l'huile obtenue à partir de pulpe seule (exemple 3).The use of 15% of core in the avocado mixture used makes it possible to increase the content of alkyl polyols and their acetylated derivatives by 7% relative to the oil obtained from the pulp alone (example 3).

Le tableau ci-dessous synthétise les résultats des différents essais 3 à 9 : N° essai Matière extraite d'avocat Teneur en alkyls polyols et dérivés acétylés Augmentation par rapport à la pulpe seule % m/m % 3 Pulpe 1,60 - 4 80% Pulpe 1,70 6 20% noyau 5 60% Pulpe 1,86 16 40% noyau 6 Avocats durs entiers dont noyau 11% 1,63 2 7 Avocats durs entiers dont noyau 29% 1,76 10 8 Avocats durs entiers dont noyau 47% 1,96 22,5 9 Avocats mous entiers dont noyau 15% 1,71 7 The table below summarizes the results of the different tests 3 to 9: Test number Material extracted from avocado Content of alkyl polyols and acetylated derivatives Increase compared to pulp alone % m / m % 3 Pulp 1.60 - 4 80% Pulp 1.70 6 20% core 5 60% Pulp 1.86 16 40% core 6 Whole hard avocados including 11% kernel 1.63 2 7 Whole hard avocados with 29% kernel 1.76 10 8 Whole hard avocados including 47% kernel 1.96 22.5 9 Whole soft avocados of which kernel 15% 1.71 7

Claims (13)

  1. A method for obtaining avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof from at least avocado seeds, said oil containing at least 0.5% alkyl polyols and/or acetylated derivatives thereof by weight, relative to the total weight of oil, said avocado seeds representing 10 to 50% by weight relative to the total weight of avocados used, said avocados used not being soft avocados having a pulp penetration resistance of less than or equal to 3 kg/cm2, said resistance being measured using a penetrometer, and said method comprising the following successive steps:
    (1) Cutting or grinding of avocados with a seed content of 10 to 50% w/w, said grinding producing a particle size distribution of the ground material between 2 and 20 mm,
    (2) High-temperature drying at a temperature between 60 and 150 °C, until a residual moisture content less than or equal to 5% is obtained,
    (3) Addition of water to the dried avocados by adding 1 to 5% water or water vapor relative to the weight of dry avocados, then
    (4) Oil extraction by mechanical pressure.
  2. The method for obtaining avocado unsaponifiable enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 1, characterized in that drying (2) is carried out at a temperature of between 80 and 120°C.
  3. The method for obtaining avocado unsaponifiable enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 1, characterized in that oil extraction (4) by mechanical pressure is carried out at a temperature between 80 and 100 °C.
  4. The method for obtaining avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 1, characterized in that avocado seeds represent 15 to 40% by weight, relative to the total weight of avocados used.
  5. The method for obtaining avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 4, characterized in that avocado seeds represent 20 to 40% by weight, relative to the total weight of avocados used.
  6. The method for obtaining avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to any one of claims 1 to 5, characterized in that the alkyl polyols are saturated, monounsaturated or polyunsaturated triols of the C17 to C21 aliphatic unbranched linear 1,2,4-trihydroxy type.
  7. The method for obtaining avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 6, characterized in that the alkyl polyols are selected from the group comprised of nonadecane-1,2,4-triol; heneicosa-cis, cis-12-15 diene-1,2,4-triol; heptadec-16-yne-1,2,4-triol; heptadec-cis-16-ene-1,2,4-triol; and mixtures thereof.
  8. Avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof, obtainable by the method according to any one of claims 1 to 7, characterized in that it contains at least 0.5% alkyl polyols or acetylated derivatives thereof by weight, relative to the total weight of oil.
  9. The avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 8, characterized in that it contains between 0.5 and 10% alkyl polyols and/or acetylated derivatives thereof by weight, relative to the total weight of oil.
  10. The avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 8 or 9, characterized in that it contains sterols and/or saturated aliphatic hydrocarbons.
  11. The avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to any one of claims 8 to 10, characterized in that it contains 1,2-dihydroxy-4-oxo-aliphatic alcohols and acetylated derivatives thereof of the "persins" type and/or alkyl furans.
  12. Avocado unsaponifiable enriched in alkyl polyols or concentrate of avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof, said concentrate containing at least 5% alkyl polyols and/or acetylated derivatives thereof by weight, relative to the total weight of the concentrate, said unsaponifiable and said oil concentrate being obtainable from avocado oil as defined in any one of claims 8 to 11, for use as a drug.
  13. The avocado unsaponifiable enriched in alkyl polyols or concentrate of avocado oil enriched in alkyl polyols and/or acetylated derivatives thereof according to claim 12, for use in the prevention and/or treatment of conjunctive tissue disorders such as arthrosis, articular pathologies such as rheumatism, or periodontal diseases such as gingivitis or periodontitis.
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WO2013098293A1 (en) * 2011-12-26 2013-07-04 Laboratoires Expanscience Use of whole soft avocados for preparing avocado oil rich in unsaponifiables

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2041594A5 (en) * 1969-04-30 1971-01-29 Expanscience
FR2678632B1 (en) * 1991-07-03 1994-09-02 Pharmascience Lab PROCESS FOR THE PREPARATION OF THE UNSAPONIFIABLE LAWYER FOR IMPROVING ITS CONTENT IN ONE OF ITS FRACTIONS SAID H
FR2798667B1 (en) 1999-09-22 2001-12-21 Pharmascience Lab PROCESS FOR THE EXTRACTION OF FURANIC COMPOUNDS AND POLYHYDROXYL FATTY ALCOHOLS FROM LAWYER, COMPOSITION BASED ON AND USE OF THESE COMPOUNDS IN THERAPEUTICS, COSMETICS AND FOOD
WO2004016106A1 (en) * 2002-07-29 2004-02-26 Laboratoires Expanscience Method for producing an unsaponifiable matter of avocado rich in furan lipids
FR2893628B1 (en) 2005-11-18 2008-05-16 Expanscience Laboratoires Sa PROCESS FOR OBTAINING REFRINED AVOCADO OIL RICH IN TRIGLYCERIDES AND OIL LIKELY OBTAINABLE BY SUCH A METHOD
CN102387838A (en) 2008-09-08 2012-03-21 多元醇生物技术有限公司 Cosmetic compositions comprising polyhydroxyltate fatty alcohols and derivatives and uses thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013098293A1 (en) * 2011-12-26 2013-07-04 Laboratoires Expanscience Use of whole soft avocados for preparing avocado oil rich in unsaponifiables

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